53137-27-2|2,4-Dimethylthiazole-5-carboxylic acid| Ambeed

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Quality Control of [ 53137-27-2 ] Purity: 98% SDS Specification

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Product Details of [ 53137-27-2 ]

CAS No. :	53137-27-2
Formula :	C₆H₇NO₂S
M.W :	157.19
SMILES Code :	O=C(C1=C(C)N=C(C)S1)O
MDL No. :	MFCD00052943
InChI Key :	MQGBARXPCXAFRZ-UHFFFAOYSA-N
Pubchem ID :	736488

Safety of [ 53137-27-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 53137-27-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.33
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	39.01
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.43 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.31
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.61
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.46
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.02
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.13
Solubility	1.16 mg/ml ; 0.00736 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.87
Solubility	0.213 mg/ml ; 0.00135 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.43
Solubility	5.85 mg/ml ; 0.0372 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.12 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.34

Application In Synthesis of [ 53137-27-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 53137-27-2 ]

[ 53137-27-2 ] Synthesis Path-Downstream 1~35

1
[ 28599-52-2 ]
[ 53137-27-2 ]

References: [1]Zhurnal Obshchei Khimii,1956,vol. 26,p. 66; engl. Ausg. S. 65.

2
[ 53137-27-2 ]
[ 100-35-6 ]
2,4-dimethyl-thiazole-5-carboxylic acid-(2-diethylamino-ethyl ester) [ No CAS ]

References: [1]Journal of the Chemical Society,1946,p. 91.

3
[ 53137-27-2 ]
[ 258521-35-6 ]

References: [1]Journal of the Chemical Society,1945,p. 601.

4
[ 7210-77-7 ]
[ 53137-27-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; In ethanol; water; for 4h;Reflux;	General procedure: The appropriate ethyl ester (1c, 3c) (5.8 mmol) was refluxed for4 h in a mixture of equal volumes of aqueous 10% NaOH (20 mL) andEthanol (20 mL). After completion of the reaction, ethanol wasevaporated under reduced pressure and the remaining solutionwasthen extracted with ethyl acetate. The organic layer was discardedwhile the aqueous layer was acidified to pH 3 with aqueous 10%hydrochloric acid. The mixturewas then evaporated under reducedpressure and the solid obtained was then dissolved in methanolwhile the remaining insoluble NaCl was discarded. Evaporating themethanol afforded the desired pure acids 1d and 3d.
	With potassium hydroxide; In methanol; water;	After 9.7 g of potassium hydroxide were added to 50 ml of methanol and 50 ml of water, 10.2 g of ethyl 2,4-dimethyl-5-thiazolecarboxylate were added dropwise thereto at room temperature. The reaction was conducted at room temperature for 1 hour, and the reaction mixture was then acidified with 2-N hydrochloric acid. After methanol was distilled off, the crystals were collected through filtration, washed with water, and dried to obtain 6.6 g of the Compound No. 2.1 of the present invention. melting point: from 220 to 225 C.

References: [1]European Journal of Medicinal Chemistry,2019,vol. 180,p. 154 - 170.
[2]Justus Liebigs Annalen der Chemie,1890,vol. 259,p. 266.
[3]Patent: US5817829,1998,A .

5
[ 7210-77-7 ]
[ 53137-27-2 ]
[ 66806-33-5 ]

References: [1]Proceedings - Indian Academy of Sciences, Section A,1945,p. 362,376.

6
[ 53137-27-2 ]
[ 111-71-7 ]
[ 113366-49-7 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.
[2]Journal of the Chemical Society. Perkin transactions I,1991,p. 2417 - 2428.

7
[ 53137-27-2 ]
[ 100-52-7 ]
[ 113366-48-6 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.
[2]Journal of the Chemical Society. Perkin transactions I,1991,p. 2417 - 2428.

8
[ 53137-27-2 ]
[ 75-03-6 ]
[ 113391-64-3 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.
[2]Journal of the Chemical Society. Perkin transactions I,1991,p. 2417 - 2428.

9
[ 53137-27-2 ]
[ 106-95-6 ]
[ 113366-47-5 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.
[2]Journal of the Chemical Society. Perkin transactions I,1991,p. 2417 - 2428.

10
[ 53137-27-2 ]
[ 98-86-2 ]
[ 113366-50-0 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.

11
[ 53137-27-2 ]
[ 74-88-4 ]
[ 113366-46-4 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.
[2]Tetrahedron Letters,1987,vol. 28,p. 3585 - 3588.
[3]Journal of the Chemical Society. Perkin transactions I,1991,p. 2417 - 2428.

12
[ 53137-27-2 ]
[ 68858-20-8 ]
[ 170117-43-8 ]
C₄₀H₅₂N₆O₆S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2995 - 3002.

13
[ 53137-27-2 ]
[ 68858-20-8 ]
[ 220784-31-6 ]
C₄₀H₅₂N₆O₅S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2995 - 3002.

14
[ 53137-27-2 ]
[ 2835-78-1 ]
2,4-Dimethyl-thiazole-5-carboxylic acid (3-benzoyl-phenyl)-amide [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5908 - 5919.

15
[ 53137-27-2 ]
[ 127000-91-3 ]
2,4-Dimethyl-thiazole-5-carboxylic acid [(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1855 - 1868.

16
2,4-dimethyl-thiazole-5-carboxylic acid methyl ester; hydrochloride [ No CAS ]
[ 53137-27-2 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

17
[ 7647-01-0 ]
[ 53137-27-2 ]
[ 173841-81-1 ]

References: [1]Journal of the Chemical Society,1945,p. 601.

18
[ 53137-27-2 ]
[ 6638-79-5 ]
[ 258261-48-2 ]

Yield	Reaction Conditions	Operation in experiment
		To a flask containing <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> (2.50 g, 15.9 mmol) was added DCM (75 mL) and DMF (3 mL) to afford a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was added and the mixture was stirred at room temperature for 2 hours. N,O-dimethylhydroxylamine hydrochloride (1.90 g, 19.9 mmol) was then added and the reaction mixture was stirred at room temperature for 18 hours, then diluted with water and 1 N NaOH and extracted with DCM (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (10-40% EtOAc-DCM) provided the title compound as a colorless oil.
		To a flask containing <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> (2.5 g, 15.9 mmol) was added DCM (75 mL) to give a suspension. DMF (3 mL) was added which resulted in a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was introduced and the mixture was stirred at room temperature for 2 hours. N,O-dimethylhydroxylamine HCl (1.9 g, 19.9 mmol) was then added and the mixture was stirred at room temperature for 18 hours, at which time the reaction mixture was diluted with water and 1 N aqueous NaOH and the aqueous portion was extracted with DCM (4*50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (10% EtOAc-DCM increasing to 40% EtOAc) provided the title compound as a colorless oil.
		intermediate 17: step aN-methoxy-N,2,4-trimethylthiazole-5-carboxamideTo a flask containing 2,4-dimethylthiazole~5~carboxylic acid (2.5 g, 15.9 mmol) was added DCM (75 mL) to give a suspension . DMF (3 mL) was added which resulted in a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was introduced and the mixture was stirred at, room temperature for 2 hours. N,0-dim.ethymydroxylamine HQ (1 .9 g, 19.9 mmol) was then added and the mixture was stirred at room temperature for 18 hours, at which time the reaction mixture was diluted with water and 5 N aqueous NaOH and the aqueous portion was extracted with DCM (4 x 50 mL). The combined organics were washed with brine, dried over a2S04, filtered and concentrated. Chromatography on silica gel (1 0% EtOAc-DCM increasing to 40% EtOAc) provided the title compound as a colorless oil.

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.
[2]Patent: US2014/107097,2014,A1 .Location in patent: Paragraph 0382; 0383.
[3]Patent: US2015/105404,2015,A1 .Location in patent: Paragraph 0283.
[4]Patent: WO2015/57203,2015,A1 .Location in patent: Page/Page column 73.

19
[ 313504-94-8 ]
[ 53137-27-2 ]
2,4-dimethyl-thiazole-5-carboxylic acid [2-(cyclohexanecarbonyl-amino)-benzothiazol-6-yl]-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3328 - 3332.

20
[ 53137-27-2 ]
5-(1H-imidazol-4-ylmethyl)-2,4-dimethyl-thiazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

21
[ 53137-27-2 ]
5-[1-(1H-imidazol-4-yl)-ethyl]-2,4-dimethyl-thiazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

22
[ 53137-27-2 ]
1-(2,4-dimethyl-thiazol-5-yl)-1-(1H-imidazol-4-yl)-ethanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

23
[ 53137-27-2 ]
5-[(1H-imidazol-4-yl)-phenyl-methyl]-2,4-dimethyl-thiazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

24
[ 53137-27-2 ]
(2,4-dimethyl-thiazol-5-yl)-(1H-imidazol-4-yl)-phenyl-methanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

25
[ 53137-27-2 ]
(2,4-dimethyl-thiazol-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

26
[ 53137-27-2 ]
[ 258261-50-6 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5064 - 5071.

27
(+/-)-trans-N-[4-phenyl-1-[2-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]acetamide dihydrochloride.dihydrate [ No CAS ]
[ 53137-27-2 ]
(+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[53137-27-2]2,4-dimethyl-5-thiazoic acid</strong>(0.080 g) and 1H-benzotriazol-1-ol (0.060 g) were added to intermediate 22 (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine was added dropwise. A solution of (CH3)2-N-(CH2)3-NN-CH2-CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. Then, the compound was isolated and purified by column chromatography (eluent: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.070 g of (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide (compound 121).

References: [1]Patent: US6346540,2002,B1 .Location in patent: Page column 22.

28
(+/-)-cis-1-[[1-[4-phenyl-2-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]carbonyl]pyrrolidine [ No CAS ]
[ 53137-27-2 ]
C₃₄H₄₂N₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[53137-27-2]2,4-dimethyl-5-thiazoic acid</strong>(0.080 g) and 1H-benzotriazol-1-ol (0.060 g) were added to intermediate 22 (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine was added dropwise. A solution of (CH3)2-N-(CH2)3-NN-CH2-CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. Then, the compound was isolated and purified by column chromatography (eluent: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.070 g of (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide (compound 121).

References: [1]Patent: US6346540,2002,B1 .Location in patent: Page column 39.

29
C₂₆H₃₄N₂O₂ [ No CAS ]
[ 53137-27-2 ]
C₃₂H₃₉N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[53137-27-2]2,4-dimethyl-5-thiazoic acid</strong>(0.080 g) and 1H-benzotriazol-1-ol (0.060 g) were added to intermediate 22 (0.100 g) in CH2Cl2 (5 ml). The mixture was stirred and cooled on an ice-bath, under N2 flow. Triethylamine was added dropwise. A solution of (CH3)2-N-(CH2)3-NN-CH2-CH3 (0.080 g) in CH2Cl2 (5 ml) was added dropwise and the reaction mixture was allowed to warm to RT, under N2. The reaction mixture was stirred overnight. Then, the compound was isolated and purified by column chromatography (eluent: (0.5% ammoniumacetate in H2O)/CH3OH/CH3CN 70/15/15 upgrading to 0/0/100). The desired fractions were collected and the solvent was evaporated, yielding 0.070 g of (+/-)-trans-N-[1-[1-[(2,4-dimethyl-5-thiazolyl)carbonyl]-2-(phenylmethyl)-4-piperidinyl]-4-phenyl-4-piperidinyl]acetamide (compound 121).

References: [1]Patent: US6346540,2002,B1 .Location in patent: Page column 37.

30
[ 53137-27-2 ]
[ 52273-77-5 ]
[ 844904-20-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); for 14h;	N- [3- (2-HYDROXYETHYL) PHENYL]-2, 4-DIMETHYL-1, 3-THIAZOLE-5-CARBOXAMIDE; 2- (3-Aminophenyl) ethanol (1.202 g, 8.76 MMOL) was added to a solution of 2, 4-dimethyl- 1, 3-thiazole-5-carboxylic acid (1.652 g, 10.51 MMOL), 1- (3-DIMETHYLAMINOPROPYL)-3- ethylcarbodiimide hydrochloride (2.015 g, 10.51 MMOL) and 1-hydroxybenzotriazole (1.420 g, 10.51 MMOL) in dry DMF (20 mL). The mixture was stirred for 14h then the DMF was removed under reduced pressure and the residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1: 1 to 1: 0) affording the title compound in 73% yield (1.772 g). MS; (ES) m/z: 277 [MH+]. C14H16N202S requires 276. 1H-NMR (300 MHz, D6-DMSO) S (ppm): 9.95 (s, 1H), 7.40-7. 50 (m, 2H), 7.19 (t, 1H), 6.92 (d, 1 H), 4.60 (t, 1 H), 5.57 (dd, 2H), 2.66 (t, 2H), 2.61 (s, 3H), 2.49 (s, 3H).

References: [1]Patent: WO2005/14552,2005,A1 .Location in patent: Page/Page column 88.

31
[ 887308-20-5 ]
[ 53137-27-2 ]
N-[5-(2-acetylamino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]-2,4-dimethyl-1,3-thiazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In acetonitrile; for 1h;Heating / reflux;	Phosphorus oxychloride (296 mg) was added to a stirred mixture of N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-l,3-thiazol-2-yl]acetamide (180 mg), 2,4-dimethylthiazole- 5-carboxylic acid (J. Med. Chem., 1999, 42, 5064; 109 mg) and acetonitrile (10 mL) that had been heated to reflux. The resultant mixture was stirred and heated to- reflux for 1 hour. The mixture was cooled to room temperature and the precipitate was collected by filtration, washed with acetonitrile and dried under vacuum. There was thus obtained the title compound(172 mg); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.39 (s, 3H), 2.62 (s, 3H), 2.68 (s, 3H), 8.21 (s, IH), 8.40 (s, IH); Mass Spectrum: M+H+ 422.

References: [1]Patent: WO2006/51270,2006,A1 .Location in patent: Page/Page column 138.

32
[ 288-32-4 ]
[ 53137-27-2 ]
5-imidazolylcarbonyl-2,4-dimethylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In tetrahydrofuran;	EXAMPLE 1 (Compound No. 1) To a solution of imidazole (2.72 g; 40 mmol) in dry tetrahydrofuran (60 ml) was added dropwise thionyl chloride (1.20 g; 10 mmol) under ice-cooling while stirring. After the resultant mixture was turned to room temperature, <strong>[53137-27-2]2,4-dimethyl-5-thiazolecarboxylic acid</strong> (1.57 g; 10 mmol) was added thereto at once, and stirring was continued for 30 minutes, whereby 5-imidazolylcarbonyl-2,4-dimethylthiazole was produced.

References: [1]Patent: US4918089,1990,A .

33
[ 288-32-4 ]
[ 53137-27-2 ]
[ 779315-19-4 ]
[ 119778-30-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With thionyl chloride; In tetrahydrofuran; water;	EXAMPLE 3 (Compound No. 3) To a solution of imidazole (2.27 g; 40 mmol) in dry tetrahydrofuran (60 ml) was added dropwise thionyl chloride (1.20 g; 10 mmol) under ice-cooling while stirring. After the resultant mixture was turned to room temperature, <strong>[53137-27-2]2,4-dimethyl-5-thiazolecarboxylic acid</strong> (1.57 g; 10 mmol) was added thereto at once, and stirring was continued for 30 minutes. To the mixture was added dropwise a solution of 2-(2-thienyl)aminoacetonitrile (1.65 g; 12 mmol) in dry tetrahydrofuran under ice-cooling, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, tetrahydrofuran was removed under reduced pressure to separate the residue. Water was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude oil. The oil was purified by silica-gel column chromatography (eluent:n-hexane:ethyl acetate=2:1 volume) to give crude crystals. Recrystallization from n-hexane/ethyl acetate gave 1.80 g of 2-(2,4-dimethylthiazole-5-carboxamido)-2-(2-thienyl)acetonitrile as colorless crystals. m.p., 127.5-128.5 C. Yield, 65%.

References: [1]Patent: US4918089,1990,A .

34
[ 288-32-4 ]
[ 53137-27-2 ]
2-(thien-3-yl)aminoacetonitrile [ No CAS ]
[ 119778-31-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With thionyl chloride; In tetrahydrofuran; water;	EXAMPLE 4 (Compound No. 4) To a solution of imidazole (2.72 g; 40 mmol) in dry tetrahydrofuran (60 ml) was added dropwise thionyl chloride (1.20 g; 10 mmol) under ice-cooling while stirring. After the resultant mixture was turned to room temperature, <strong>[53137-27-2]2,4-dimethyl-5-thiazolecarboxylic acid</strong> (1.57 g; 10 mmol) was added thereto at once, and stirring was continued for 30 minutes. To the mixture was added dropwise a solution of 2-(3-thienyl)aminoacetonitrile (1.65 g; 12 mmol) in dry tetrahydrofuran under ice-cooling, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, tetrahydrofuran was removed under reduced pressure to separate the residue. Water was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude oil. The oil was purified by silica-gel column chromatography (eluent:n-hexane:ethyl acetate=2:1 volume) to give crude crystals. Recrystallization from n-hexane/ethyl acetate gave 1.95 g of 2-(2,4-dimethylthiazole-5-carboxamido)-2-(3-thienyl)acetonitrile as colorless crystals. m.p., 94-95 C. Yield, 70%.

References: [1]Patent: US4918089,1990,A .

35
[ 53137-27-2 ]
[ 119778-43-7 ]

Yield	Reaction Conditions	Operation in experiment
95.0% and 98.0%	In 5,5-dimethyl-1,3-cyclohexadiene;	EXAMPLE 1 In a 300-ml three-neck flask, 7.9 g (0.5) mole) of 2,4-dimethylthiazole-5carboxylic acid were suspended in 200 ml of xylene and under heating and reflux, phosgene was blown at a flow rate of 340 ml/hr for 12 hours (0.18 mole). After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 8.2 g of <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> chloride. Its purity and yield were 95.0% and 98.0%, respectively.
97.5% and 98.0%	In N,N-dimethyl-formamide; toluene;	EXAMPLE 10 In a similar apparatus to Example 1, 15.7 g (0.1 mole) of <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> were suspended in 100 ml of toluene, followed by the addition of 0.1 g of N,N-dimethylformamide. Under heating and reflux, phosgene was blown at a rate of 1.3 l/hr for 5 hours (0.29 mole). After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 17.2 g of <strong>[53137-27-2]2,4-dimethylthiazole-5-carboxylic acid</strong> chloride. Its purity and yield were 97.5% and 98.0%, respectively.
	With thionyl chloride; In dichloromethane; at 20℃; for 1h;	The <strong>[53137-27-2]2,4-dimethyl-thiazole-5-carboxylic acid</strong> (50.0mg, 0.318mmol) and dichloromethane (2mL) into 10mL round bottom flask at 0 was added thionyl chloride (378.43mg, 3.18 mmol) was stirred at room temperature for 1 hour. TLC showed the reaction was complete. The mixture was concentrated to give the title compound as a black solid, used without purification in the next reaction.

References: [1]Patent: US5136042,1992,A .
[2]Patent: US5136042,1992,A .
[3]Patent: CN105461711,2016,A .Location in patent: Paragraph 0312; 0317; 0318.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 53137-27-2 ]

Carboxylic Acids

A977066 [119778-44-8]

4-Ethyl-2-methylthiazole-5-carboxylic acid

Similarity: 0.91

A380806 [20485-41-0]

4-Methylthiazole-5-carboxylic acid

Similarity: 0.89

A165993 [117724-63-7]

2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid

Similarity: 0.87

A156337 [40004-69-1]

2-Methyl-5-thiazolecarboxylic acid

Similarity: 0.81

A519243 [67899-00-7]

2-Amino-4-methylthiazole-5-carboxylic acid

Similarity: 0.79

Related Parent Nucleus of
[ 53137-27-2 ]

Thiazoles

A977066 [119778-44-8]

4-Ethyl-2-methylthiazole-5-carboxylic acid

Similarity: 0.91

A380806 [20485-41-0]

4-Methylthiazole-5-carboxylic acid

Similarity: 0.89

A165993 [117724-63-7]

2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid

Similarity: 0.87

A132435 [81569-44-0]

Methyl 4-methylthiazole-5-carboxylate

Similarity: 0.85

A123688 [50382-32-6]

(2,4-Dimethylthiazol-5-yl)methanol

Similarity: 0.83

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CAS No.: 53137-27-2

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