121246-96-6|3-Chloropyrazine-2-carbaldehyde| Ambeed

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Quality Control of [ 121246-96-6 ] Purity: 95% SDS Specification

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Product Details of [ 121246-96-6 ]

CAS No. :	121246-96-6
Formula :	C₅H₃ClN₂O
M.W :	142.54
SMILES Code :	O=CC1=NC=CN=C1Cl
MDL No. :	MFCD07371660
InChI Key :	QRVSQUNWTBLLOC-UHFFFAOYSA-N
Pubchem ID :	17962962

Safety of [ 121246-96-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405

Computational Chemistry of [ 121246-96-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	32.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.85 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.69
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	0.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.94
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.	-0.84
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	1.72
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.61

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.49
Solubility	4.6 mg/ml ; 0.0323 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.01
Solubility	13.9 mg/ml ; 0.0974 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-2.19
Solubility	0.916 mg/ml ; 0.00643 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	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.	-6.79 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	1.0 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)	1.63

Application In Synthesis of [ 121246-96-6 ]

* 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 [ 121246-96-6 ]

[ 121246-96-6 ] Synthesis Path-Downstream 1~35

1
[ 14508-49-7 ]
[ 109-94-4 ]
[ 121246-96-6 ]

References: [1]Synthesis,1988,p. 881 - 884.

2
2-chloro-3-[1,3]dithian-2-yl-pyrazine [ No CAS ]
[ 121246-96-6 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 31 - 34.

3
[ 109-01-3 ]
[ 121246-96-6 ]
[ 870134-04-6 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate; In 1,4-dioxane; for 1h;Heating / reflux;	PREPARATION 14; EPO <DP n="71"/>4-Methyl-3,4,5,6-tetrahvdro-2H-?,2'lbipyrazinyl-3'-carbaldehvde;.S-Chloro-pyrazine^-carb-aldehyde (Turck, et al., Synthesis 1988, 881-4) (6.01 g, -40 mmol), N-methylpiperazine (6.6 mL, 59.4 mmol) and K2CO3 (8.3g, 60.0 mmol) were refluxed for 1h in dioxane (250 mL). After cooling, the mixture was filtered and concentrated to an orange oil. This was dissolved in EtOAc (500 mL) and washed with water (4x150 mL) and brine, dried (MgSO4) and concentrated. Chromatography with 5% MeOH/ CH2CI2 gave 3.34 g (40%) of PP14 as a dark red oil : NMR (CDCI3) 9.94 (s, 1 H), 8.18 (d, J= 2.1 Hz, 1 H), 8.08 (d, J = 2.1 Hz, 1 H), 3.59 (t, J= 5.2 Hz, 4H), 2.53 (t, J = 5.0 Hz, 4H), 2.32 (s, 3H).
	With potassium carbonate; In 1,4-dioxane; at 100℃; for 1.5h;	Preparation 1; 4-Methyi-3,4,5,6-tetrahydro-2H-[1,2'lbip(at)rrazinyl-3'-carbaldehyde; n-BuLi (56 mmol, 22.4 mL, 2.5 M in hexanes) was added to tetrahydrofuran (300 mL) cooled to-78 C followed by the addition of 2,2-6,6-tetramethylpiperidine (52 mmol, 8.71 mL). The solution was removed from the cooling bath and stirred for 30 minutes and then cooled back to -78C. 2-chloropyrazine (40 mmol, 3.65 mL) was added dropwise, and the solution turned a reddish-brown color. After stirring 30 minutes, methylformate (60 mmol, 3.7 mL) was added and the reaction mixture was stirred for 2.25 hrs at -78C. Acetic acid (8 mL) was added and the mixture was warmed to 0C, was washed 3 times with 1: 1 brine-water, dried over sodium sulfate, and then concentrated in vacuo. The residue was dissolved in 1,4- dioxane (250 mL) and 1-methylpiperazine (60 mmol, 6.6mL) and potassium carbonate solution (8.28g in 60 mL of water) were added and the mixture was heated at 100C for 1.5 hours. After cooling to room temperature, the mixture was filtered through a Celite pad which was then washed with chloroform. The filtrate was concentrated in vacuo and purified by silica gel chromatography (100: 1:1 chloroform-methanol-ammonium hydroxide) to yield 3.3 g (40% yield for two steps) of 4-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-carbaldehyde; ¹3C NMR (100 MHz, CDC13) d 191.7,154.3, 145.3,134.5, 133.2, 55.1, 48.7, 46.3; MS (AP/CI) 207.2 (M+H)+.

References: [1]Patent: WO2006/48727,2006,A1 .Location in patent: Page/Page column 69-70.
[2]Patent: WO2005/113535,2005,A2 .Location in patent: Page/Page column 24.

4
[ 109-94-4 ]
[ 121246-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		2,2,6,6-Tetramethylpiperidine (19.7ml, 117mmol) was added to a solution of n-butyl lithium (69.3ml of a 1.6M solution in hexane, lllmmol) in anhydrous THF (200ml) at -760C under an atmosphere of nitrogen, keeping the reaction temperature below -7O0C. The reaction mixture was stirred at -7O0C for 15 minutes then allowed to warm to O0C and stirred for a further 30 minutes before being cooled to -760C. 2-Chloropyrazine (1Og, 87.3mmol) was added dropwise such that the reaction temperature was kept below -7O0C. The reaction mixture was then stirred at -700C for 30 minutes. Ethyl formate (7.5ml, 98mmol) was then added such that the reaction temperature was kept below -700C. The reaction mixture was then stirred at -7O0C for 1.5 hours. Glacial acetic acid (13ml,.218mmol) was added at -7O0C and the mixture then allowed to warm to ambient temperature and the volatiles were removed by evaporation. The residue dissolved in ethanol (100ml) and hydroxylamine (6.83g, 105mmol) and triethylamine (24.2ml, 175mmol) were added. The mixture was heated at 500C for 18 hours and the volatiles were then removed by evaporation. The residue was dissolved in diethylether and any remaining insoluble material was removed by filtration. The filtrate was washed with water, the solvent removed from the organic layer by evaporation and the residue purified by chromatography on silica gel eluting with DCM, then with diethylether / DCM (1:4) and finally with EtOAc to give 3-chloropyrazine-2- carboxaldehyde oxime (5.21g, 37.9%) as a solid; NMR Spectrum 8.37 (s, IH), 8.50 (d, IH), 8.70 (d, IH), 12.25 (s, IH).

References: [1]Patent: WO2006/106307,2006,A1 .Location in patent: Page/Page column 88.

5
[ 121246-96-6 ]
[ 911816-14-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine; triethylamine; In ethanol; at 50℃; for 18h;	2,2,6,6-Tetramethylpiperidine (19.7ml, 117mmol) was added to a solution of n-butyl lithium (69.3ml of a 1.6M solution in hexane, lllmmol) in anhydrous THF (200ml) at -760C under an atmosphere of nitrogen, keeping the reaction temperature below -7O0C. The reaction mixture was stirred at -7O0C for 15 minutes then allowed to warm to O0C and stirred for a further 30 minutes before being cooled to -760C. 2-Chloropyrazine (1Og, 87.3mmol) was added dropwise such that the reaction temperature was kept below -7O0C. The reaction mixture was then stirred at -700C for 30 minutes. Ethyl formate (7.5ml, 98mmol) was then added such that the reaction temperature was kept below -700C. The reaction mixture was then stirred at -7O0C for 1.5 hours. Glacial acetic acid (13ml,.218mmol) was added at -7O0C and the mixture then allowed to warm to ambient temperature and the volatiles were removed by evaporation. The residue dissolved in ethanol (100ml) and hydroxylamine (6.83g, 105mmol) and triethylamine (24.2ml, 175mmol) were added. The mixture was heated at 500C for 18 hours and the volatiles were then removed by evaporation. The residue was dissolved in diethylether and any remaining insoluble material was removed by filtration. The filtrate was washed with water, the solvent removed from the organic layer by evaporation and the residue purified by chromatography on silica gel eluting with DCM, then with diethylether / DCM (1:4) and finally with EtOAc to give 3-chloropyrazine-2- carboxaldehyde oxime (5.21g, 37.9%) as a solid; NMR Spectrum 8.37 (s, IH), 8.50 (d, IH), 8.70 (d, IH), 12.25 (s, IH).

References: [1]Patent: WO2006/106307,2006,A1 .Location in patent: Page/Page column 88.

6
[ 14508-49-7 ]
[ 68-12-2 ]
[ 121246-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		A flame dried and cooled 100 mL round bottom flask was charged with 2,2,6,6-tetramethylpiperidine (2.5 mL, 14.96 mmol) and anhydrous THF (25 mL) under a nitrogen atmosphere. The contents were cooled to -78 C. and n-butyllithium (2.5 M in hexane, 5.7 mL, 14.28 mmol) was added dropwise over a 5 minute period. The reaction mixture was stirred at -78 C. for 5 minutes, bought to 0 C. and stirred at 0 C. for 25 minutes. The reaction mixture was recooled to -78 C. and 2-chloropyrazine (0.78 g, 1 mL, 6.8 mmol) was added over a 3 minute period. After 30 minutes at -78 C., anhydrous DMF (0.99 mL, 13.6 mmol) was added over 3 minutes and the contents stirred at -78 C. for a further 30 minutes. The reaction mixture was bought to 0 C., stirred at 0 C. for 15 minutes, recooled to -78 C. and quenched by the addition of acetic acid (4 mL) in THF (10 mL). The reaction mixture was stirred at room temperature for 10 minutes and partitioned between ethyl acetate (60 mL) and brine (30 mL). The ethyl acetate layer is separated, dried over sodium sulfate, concentrated under reduced pressure and purified by silica gel flash chromatography using dichloromethane and ethyl acetate (9.5:0.5, 400 mL) to yield the title compound a (950 mg). 1H-NMR of the compound was consistent with the desired structure.

References: [1]Patent: US2008/275052,2008,A1 .Location in patent: Page/Page column 21.

7
[ 14508-49-7 ]
[ 107-31-3 ]
[ 121246-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 1; 4-Methyi-3,4,5,6-tetrahydro-2H-[1,2'lbip(at)rrazinyl-3'-carbaldehyde; n-BuLi (56 mmol, 22.4 mL, 2.5 M in hexanes) was added to tetrahydrofuran (300 mL) cooled to-78 C followed by the addition of 2,2-6,6-tetramethylpiperidine (52 mmol, 8.71 mL). The solution was removed from the cooling bath and stirred for 30 minutes and then cooled back to -78C. 2-chloropyrazine (40 mmol, 3.65 mL) was added dropwise, and the solution turned a reddish-brown color. After stirring 30 minutes, methylformate (60 mmol, 3.7 mL) was added and the reaction mixture was stirred for 2.25 hrs at -78C. Acetic acid (8 mL) was added and the mixture was warmed to 0C, was washed 3 times with 1: 1 brine-water, dried over sodium sulfate, and then concentrated in vacuo. The residue was dissolved in 1,4- dioxane (250 mL) and 1-methylpiperazine (60 mmol, 6.6mL) and potassium carbonate solution (8.28g in 60 mL of water) were added and the mixture was heated at 100C for 1.5 hours. After cooling to room temperature, the mixture was filtered through a Celite pad which was then washed with chloroform. The filtrate was concentrated in vacuo and purified by silica gel chromatography (100: 1:1 chloroform-methanol-ammonium hydroxide) to yield 3.3 g (40% yield for two steps) of 4-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-carbaldehyde; ¹3C NMR (100 MHz, CDC13) d 191.7,154.3, 145.3,134.5, 133.2, 55.1, 48.7, 46.3; MS (AP/CI) 207.2 (M+H)+.

References: [1]Patent: WO2005/113535,2005,A2 .Location in patent: Page/Page column 24.

8
[ 121246-96-6 ]
[ 1066-54-2 ]
C₁₀H₁₂N₂OSi [ No CAS ]

References: [1]Beilstein Journal of Organic Chemistry,2010,vol. 6.

9
[ 121246-96-6 ]
[ 89283-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In methanol; at 20℃; for 1h;	To a solution of <strong>[121246-96-6]3-chloropyrazine-2-carbaldehyde</strong> (700mg, 4.91 mmol) in methanol (10ml) was dropwise NaBH4 (223mg, 5.89mmol). The reaction mixture was stirred at room temperature for 1 hr, and the reaction was terminated with a saturated aqueous ammonium solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in a vacuum.

References: [1]Patent: WO2014/157994,2014,A1 .Location in patent: Page/Page column 131.

10
[ 121246-96-6 ]
[ 45660-95-5 ]

References: [1]Patent: WO2014/157994,2014,A1 .

11
[ 121246-96-6 ]
(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[(3-chloropyrazin-2-yl)methyl]oxazolidin-2-one [ No CAS ]

References: [1]Patent: WO2014/157994,2014,A1 .

12
[ 121246-96-6 ]
(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[3-(cyclohexylamino)pyrazin-2-yl]methyl}oxazolidin-2-one [ No CAS ]

References: [1]Patent: WO2014/157994,2014,A1 .

13
[ 121246-96-6 ]
(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[6-bromo-3-(cyclohexylamino)pyrazin-2-yl]methyl}oxazolidin-2-one [ No CAS ]

References: [1]Patent: WO2014/157994,2014,A1 .

14
[ 121246-96-6 ]
(1S,3R)-methyl 3-(((3-chloropyrazin-2-yl)(4-phenoxyphenyl)methyl)carbamoyl)-2,2-di methylcyclobutanecarboxylate [ No CAS ]