85333-43-3|8-Chloro-2-methylimidazo[1,2-a]pyrazine| Ambeed

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Quality Control of [ 85333-43-3 ] Purity: 97% SDS Specification

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Product Details of [ 85333-43-3 ]

CAS No. :	85333-43-3
Formula :	C₇H₆ClN₃
M.W :	167.60
SMILES Code :	ClC1=NC=C[N]2C1=NC(=C2)C
MDL No. :	MFCD09999202
InChI Key :	ZZPUXAQVYFAAMQ-UHFFFAOYSA-N
Pubchem ID :	13389082

Safety of [ 85333-43-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 85333-43-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	42.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	30.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.91
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	2.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.69
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.	0.44
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	1.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.53

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.78
Solubility	0.281 mg/ml ; 0.00167 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.	-2.31
Solubility	0.816 mg/ml ; 0.00487 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	-2.71
Solubility	0.328 mg/ml ; 0.00195 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	Yes
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	Yes
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.	-5.87 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.	0.55

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)	2.08

Application In Synthesis of [ 85333-43-3 ]

* 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 [ 85333-43-3 ]

[ 85333-43-3 ] Synthesis Path-Downstream 1~35

1
[ 6863-73-6 ]
[ 78-95-5 ]
[ 85333-43-3 ]

Yield	Reaction Conditions	Operation in experiment
68%		A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375.8 mmol) and chloroacetone (120 ml, 1504.5 mmol) was stirred at 90 C for 16 h. in a sealed tube protected from light. After cooling to RT, Et20 was added and the solid formed was filtered off, washed with further Et20, suspended in a saturated solution of sodium carbonate and extracted with DCM. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et20 to yieldintermediate 4 (43.2 g, 68%) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6 C (WRS-2A).
68%		Example A4 8-Chloro-2-methyl-imidazol[1,2-a]pyrazine A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375.8 mmol) and chloroacetone (120 ml, 1504.5 mmol) was stirred at 90 C. for 16 h. in a sealed tube protected from light. After cooling to RT, Et2O was added and the solid formed was filtered off, washed with further Et2O, suspended in a saturated solution of sodium carbonate and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et2O to yield intermediate 4 (43.2 g, 68%) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6 C. (WRS-2A).
68%	at 90℃; for 16h;Sealed tube; Darkness;	A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375 8 mmol) and chloroacetone (120 ml, 1504.5 mmol) was stirred at 90 C. for 16 h. in a sealed tube protected from light. After cooling to RT, Et2O was added and the solid formed was filtered off, washed with further Et2O, suspended in a saturated solution of sodium carbonate and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from Et2O to yield intermediate 6 (43.2 g, 68%) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6 C. (WRS-2A).

53%	at 90℃; for 16h;Sealed tube;	A mixture of 3-chloropyrazin-2-amine (2 g, 15.4 mmol) and 1-chloropropan-2-one (4mL) was heated to 90 C for 16 h in a sealed tube. The reaction mixture was then cooled to roomtemperature and the solid formed was filtered, washed with ether and dried to get the titled compound (1.4 g, 53%). LC-MS: 168.3 [M+Hj.
7.7%	In methanol; at 88℃;Heating / reflux;	A solution of 2-amino-3-chloropyrazine (1Og, 77.5mmol), chloroacetone (3OmL, 387mmol) in MeOH (25ml_) is refluxed overnight at 88C. It is then stirred for Ih at O0C and any solid that forms, is filtered off and washed twice with MeOH (5ml_). The mother liq. are evaporated, diluted with EtOAc, and washed with HCI 2N, water and brine. The water and HCI mother liq. are evaporated to give a yellow solid that is neutralized with a saturated solution of K2CO3 in water, extracted with DCM, dried with MgSO4 anh. filtered and concentrated. The crude material is purified by column chromatography using a gradient of (DCM/MeOH: 1/0 to 99/1) to give 8-Chloro-2-methyl-imidazo[l,2-a]pyrazine as an orange solid (1.02g, 7.7%).
	at 90℃; for 16h;Sealed tube;	A mixture of 3-chloro-pyrazin-2-ylamine (48.7 g, 375.8 mmol) and chloroacetone (120ml, 1504.5 mmol) was stirred at 90 oc for 16 h. in a sealed tube protected from light. After cooling toRT, Et20 was added and the solid formed was filtered off, washed withfurther Et20, suspended in a saturated solution of sodium carbonate and extracted withDCM. The organic layer was separated, dried (Na2S04), filtered and the solventsevaporated in vacuo. The crude product was precipitated from Et20 to yieldintermediate 6 (43.2 g, 68%) as a white solid which was used in the next step without further purification. m.p. 133.5-138.6 oc (WRS-2A).

References: [1]Patent: WO2011/110545,2011,A1 .Location in patent: Page/Page column 73-74.
[2]Patent: US2012/329792,2012,A1 .Location in patent: Page/Page column 33-34.
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 4196 - 4212.
[4]Patent: US2015/203498,2015,A1 .Location in patent: Paragraph 0167; 0168.
[5]Patent: WO2016/185342,2016,A1 .Location in patent: Page/Page column 39.
[6]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.
[7]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.
[8]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 67.
[9]Patent: WO2014/9305,2014,A1 .Location in patent: Page/Page column 31.

2
[ 103-63-9 ]
[ 85333-43-3 ]
[ 110206-70-7 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2031 - 2046.

3
[ 6863-73-6 ]
[ 126-38-5 ]
[ 85333-43-3 ]

Yield	Reaction Conditions	Operation in experiment
54%		A mixture of l-bromo-2, 2-dimethoxypropane (42.4 g, 231.5 mmol) and conc. HC1 (890 uL, 28.9 mmol) in water (6.25 mL) was heated to 90C, for 15 min, cooled to r. t. and quenched with NaHC03. 2-Amino-3-chloropyrazine (Compound I in Scheme 1,0. 2 g, 1.54 mmol) was added and the resultant mixture was heated to 90C for 2h 30 min. The cooled reaction mixture was partitioned between 2M NaHC03 aq (100 mL) and dichloromethane (100 mL). The aqueous layer was separated and extracted with dichloromethane (5 x 100 mL). The combined organic extracts were dried over anhydr. Na2S04 and concentrated in vacuo to yield the crude title compound. Purification by recrystallization from the minimum amount of hot dichloromethane provided 7.0 g (54 % yield) of the pure title compound.'H NMR (CH30H-d4) 8 8. 38 (d, J 4. 5 Hz, 1H), 7.88 (s, 1H), 7.65 (d, J4.5 Hz, 1H), 2.49 (s, 3H); MS (ESI) 167. 8 ([M+H] +, Cl35), 169.8 ([M+H] +, C137)

References: [1]Patent: WO2005/34837,2005,A2 .Location in patent: Page/Page column 41.

4
[ 85333-43-3 ]
[ 850406-38-1 ]

Yield	Reaction Conditions	Operation in experiment
89%		A mixture of 8-chloro-2-methylimidazo [1, 2-a] pyrazine (Compound IIa in Scheme 1, 2.5 g, 15 mmol) and conc. HC1 (1.5 mL, 1.2 eq. , 18 mmol) in water (20 mL) was refluxed for 3 h. The cooled reaction mixture was concentrated in vacuo and the residual solid was extracted with hot ethanol (4 x 100 mL). The combined ethanolic filtrates were treated with KHC03 (1. 8 g, 1.2 eq. , 18 mmol), the resultant insoluble material was filtered and the filtrate was concentrated in vacuo to provide 2.0 g (89% yield) of the title compound. 1H NMR (DMSO-d6) S 12.15 (br s, 1H), 7.90 (s, 1H), 7. 68 (d, J 5. 5 Hz, 1H), 7.20 (t, J5. 5 Hz, 1H), 2.38 (s, 3H)

References: [1]Patent: WO2005/34837,2005,A2 .Location in patent: Page/Page column 42.

5
[ 85333-43-3 ]
[ 1124321-36-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-Bromosuccinimide; In dichloromethane; at 20℃; for 2h;	To a solution of 8-Chloro-2-methyl-imidazo[l,2-a]pyrazine (0.7 g, 4.18 mmol) in DCM (20 ml) is added N-bromosuccinimide (0.74 g, 4.18 mmol) and the reaction stirred at room temperature for 2h. After this time the solution is washed with saturated aqueous solution of Na2CO3 (2 x 20 ml), dried (MgSO4), filtered and concentrated in vacuo to give 3-bromo-8-chloro- 2-methyl-imidazo[l,2-a]pyrazine (0.771 g, 75 %).

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.
[2]Patent: WO2009/24585,2009,A2 .Location in patent: Page/Page column 67-68.
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 4196 - 4212.

6
[ 1692-15-5 ]
[ 85333-43-3 ]
[ 1334167-23-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate; triphenylphosphine;palladium diacetate; In 1,4-dioxane; water; at 80℃; for 16h;	Palladium (II) acetate (0.47 g, 2.09 mmol) was added to a stirred solution of intermediate 4 (5.0 g, 29.83 mmol), 4-pyridineboronic acid (8.15 g, 59.67 mmol) and triphenylphosphine (0.78 g, 2.98 mmol) in a mixture of 1,4-dioxane (125 ml) and a 1.5 M solution of potassium carbonate (74.5 ml, 111.87 mmol). The mixture was stirred at 80 C for 16h. and then the solvents were evaporated in vacuo. The mixture was partitioned between water and DCM and the organic layer was separated, dried(Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM 5/95). The desired fractions were collected and evaporated in vacuo to yield intermediate 11 (4.2 g, 53%) as a pale brown solid.
53%	With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; at 80℃; for 16h;	Example A11 2-Methyl-8-pyridin-4-yl-imidazol[1,2-a]pyrazine Palladium (II) acetate (0.47 g, 2.09 mmol) was added to a stirred solution of intermediate 4 (5.0 g, 29.83 mmol), 4-pyridineboronic acid (8.15 g, 59.67 mmol) and triphenylphosphine (0.78 g, 2.98 mmol) in a mixture of 1,4-dioxane (125 ml) and a 1.5 M solution of potassium carbonate (74.5 ml, 111.87 mmol). The mixture was stirred at 80 C. for 16 h. and then the solvents were evaporated in vacuo. The mixture was partitioned between water and DCM and the organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM 5/95). The desired fractions were collected and evaporated in vacuo to yield intermediate 11 (4.2 g, 53%) as a pale brown solid.

References: [1]Patent: WO2011/110545,2011,A1 .Location in patent: Page/Page column 76.
[2]Patent: US2012/329792,2012,A1 .Location in patent: Page/Page column 35.
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 4196 - 4212.

7
[ 85333-43-3 ]
[ 1334167-35-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-iodo-succinimide; acetic acid; In dichloromethane; at 0 - 20℃; for 16h;	N-Iodosuccinimide (14.1 g, 62 mmol) was added to a stirred solution of intermediate 4 (9.58 g, 57 mmol) in a mixture of DCM and acetic acid at 0 C. The mixture was allowed to warm to RT and then stirred for 16 h. The mixture was diluted with further DCM and washed with a saturated solution of sodium carbonate and sodium thiosulfite. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was precipitated from diisopropyl ether to yieldintermediate 25 (16 g, 97%) as a pale brown solid which was used in the next step without further purification.
97%	With N-iodo-succinimide; acetic acid; In dichloromethane; at 0 - 20℃; for 16h;	Example A25 3-Iodo-<strong>[85333-43-3]8-chloro-2-methyl-imidazo[1,2-a]pyrazine</strong> N-Iodosuccinimide (14.1 g, 62 mmol) was added to a stirred solution of intermediate 4 (9.58 g, 57 mmol) in a mixture of DCM and acetic acid at 0 C. The mixture was allowed to warm to RT and then stirred for 16 h. The mixture was diluted with further DCM and washed with a saturated solution of sodium carbonate and sodium thiosulfite. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from diisopropyl ether to yield intermediate 25 (16 g, 97%) as a pale brown solid which was used in the next step without further purification.
97%	With N-iodo-succinimide; acetic acid; In dichloromethane; at 0 - 20℃; for 16h;	N-Iodosuccinimide (14.1 g, 62 mmol) was added to a stirred solution of intermediate 6 (9.58 g, 57 mmol) in a mixture of DCM and acetic acid at 0 C. The mixture was allowed to warm to RT and then stirred for 16 h. The mixture was diluted with further DCM and washed with a saturated solution of sodium carbonate and sodium thiosulfite. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was precipitated from diisopropyl ether to yield intermediate 7 (16 g, 97%) as a pale brown solid which was used in the next step without further purification.

With N-iodo-succinimide; In dichloromethane; acetic acid; at 0 - 20℃; for 16h;

N-Iodosuccinimide (14.1 g, 62 mmol) was added to a stirred solution of intermediate 6(9.58 g, 57 mmol) in a mixture ofDCM and acetic acid at 0 C. The mixture was allowed to warm toRT and then stirred for 16 h. The mixture was diluted with further DCM and washed with a saturated solution of sodium carbonate and sodium thiosulfite.The organic layer was separated, dried (Na2S04), filtered and the solvents evaporatedin vacuo. The crude product was precipitated from diisopropyl ether to yieldintermediate 7 (16 g, 97%) as a pale brown solid which was used in the next step without further purification.

References: [1]Patent: WO2011/110545,2011,A1 .Location in patent: Page/Page column 80.
[2]Patent: US2012/329792,2012,A1 .Location in patent: Page/Page column 37.
[3]Patent: US2015/203498,2015,A1 .Location in patent: Paragraph 0169; 0170.
[4]Patent: WO2014/9305,2014,A1 .Location in patent: Page/Page column 32.
[5]Journal of Medicinal Chemistry,2015,vol. 58,p. 978 - 993.

8
[ 85333-43-3 ]
[ 1124321-37-4 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.

9
[ 85333-43-3 ]
[ 1436383-97-9 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.

10
[ 85333-43-3 ]
[ 1124320-61-1 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.

11
[ 85333-43-3 ]
[ 1124321-01-2 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.

12
[ 85333-43-3 ]
[ 1436383-95-7 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 585 - 589.

13
[ 85333-43-3 ]
[ 1334167-55-3 ]

References: [1]Patent: WO2014/9305,2014,A1 .
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 978 - 993.
[3]Patent: US2015/203498,2015,A1 .

14
[ 85333-43-3 ]
2-methoxy-1-[5-(2-methyl-8-morpholin-4-ylimidazo[1,2-a]pyrazin-3-yl)pyridin-2-yl]ethanol [ No CAS ]

References: [1]Patent: WO2014/9305,2014,A1 .

15
[ 85333-43-3 ]
[ 1537868-60-2 ]

References: [1]Patent: WO2014/9305,2014,A1 .
[2]Patent: US2015/203498,2015,A1 .

16
[ 1692-25-7 ]
[ 85333-43-3 ]
[ 1334167-24-6 ]