77168-85-5|Methyl 5-chloro-6-methylpyrazine-2-carboxylate| Ambeed

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Quality Control of [ 77168-85-5 ] Purity: 97% SDS Specification

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Product Details of [ 77168-85-5 ]

CAS No. :	77168-85-5
Formula :	C₇H₇ClN₂O₂
M.W :	186.60
SMILES Code :	COC(=O)C1=CN=C(Cl)C(C)=N1
MDL No. :	MFCD18633146
InChI Key :	GGNGFNQPYMKDDR-UHFFFAOYSA-N
Pubchem ID :	12619146

Safety of [ 77168-85-5 ]

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

Computational Chemistry of [ 77168-85-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	43.29
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.08 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.81
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	1.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.22
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.	0.08
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	1.81
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.07
Solubility	1.58 mg/ml ; 0.00846 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.	-2.03
Solubility	1.76 mg/ml ; 0.00944 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	-2.73
Solubility	0.345 mg/ml ; 0.00185 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.	-6.49 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)	2.17

Application In Synthesis of [ 77168-85-5 ]

* 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 [ 77168-85-5 ]

[ 77168-85-5 ] Synthesis Path-Downstream 1~35

1
[ 77168-85-5 ]
[ 77168-86-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.

2
[ 77168-84-4 ]
[ 77168-85-5 ]

Yield	Reaction Conditions	Operation in experiment
52%	With trichlorophosphate; In N,N-dimethyl-formamide;	Example 47 METHYL 5-CHLORO-6-METHYL-2-PYRAZINE CARBOXYLATE To a solution of methyl 4,5-dihydro-6-methyl-5-oxo-2-pyrazine carboxylate (M. Mano, T. Seo, K. Imai, Chem. Pharm. Bull 10:3057-3063, 1980) in DMF (20 mL) was added POCl3 (20 mL). The reaction was refluxed for 0.5 h and then poured into ice. The aqueous layer was extracted with CHCl3 dried (MgSO4) and concentrated. The residue was chromatographed (SiO2, CHCl3) to provide the title compound (2.34 g, 52% yield); m.p. 49-50 C.
	With N,N-dimethyl-formamide; trichlorophosphate; at 5 - 110℃; for 3.0h;	Step 4, methyl 5-chloro-6-methylpyrazine-2-carboxylate To a stirred solution of methyl 6- methyl-5-oxo-4,5-dihydropyrazine-2-carboxylate (75 g, 0.446 mol) in phosphorous oxychloride (375 mL) was added DMF (5 mL) at 5-10 C. The reaction mixture was heated to 110 C for 3 h. Then the POCf was distilled off from the reaction mixture. The resulting residue was quenched with ice-cold water (300 mL) and extracted with dichloromethane (3 x 500 mL). The combined organic layers were washed with water (500 mL), brine (300 mL), dried over anhydrous sodium sulfate and concentrated to afford a crude residue. The crude residue was adsorbed on 150 g of 100-200 silica gel, which was then loaded over a pre-packed column with silica gel and gradient eluted with 12 % ethyl acetate/petroleum ether to 18 % ethyl acetate/petroleum ether to give the title compound

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.
[2]Patent: US5811428,1998,A .
[3]Patent: WO2019/99315,2019,A1 .Location in patent: Page/Page column 60; 61.

3
[ 77168-82-2 ]
[ 77168-85-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.

4
[ 77168-83-3 ]
[ 77168-85-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.
[2]Patent: WO2019/99315,2019,A1 .

5
[ 77168-85-5 ]
[ 77168-87-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.

6
[ 77168-85-5 ]
[ 77168-88-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.

7
[ 57005-61-5 ]
[ 77168-85-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.
[3]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.
[4]Patent: WO2019/99315,2019,A1 .

8
[ 77168-81-1 ]
[ 77168-85-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.
[2]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3057 - 3063.

9
[ 7732-18-5 ]
[ 584-08-7 ]
[ 77168-85-5 ]
5-chloro-6-methylpyrazine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		Example 48 5-CHLORO-6-METHYL-2-PYRAZINECARBOXYLIC ACID A mixture of <strong>[77168-85-5]methyl 5-chloro-6-methyl-2-pyrazine carboxylate</strong> (0.16 g, 0.86 mmol), K2 CO3 (0.31 g, 2.18 mmol) and H2 O was stirred for 2 h at room temperature. The reaction was filtered and acidified (20percent HCl), and the resulting solid collected to provide the title compound (0.057 g, 39percent yield); m.p. 116°-117° C.

References: [1]Patent: US5811428,1998,A .

10
C₂H₂O₄*C₁₂H₂₄N₂O₂ [ No CAS ]
[ 77168-85-5 ]
[ 1161772-04-8 ]

Yield	Reaction Conditions	Operation in experiment
		Water (500ml) and Compound ll-a (85.0 g) were changed into a flask and the mixture was agitated for 10 to 20 minutes. Potassium Phosphate (127g) and toluene (500ml) were charged into the reaction. The batch was agitated until all solids were dissolved. The aqueous was split and the organic phase was concentrated to about 170ml or less if possible under vacuum. 1-Methyl-2- pyrrolidinone (NMP) (204 ml) was charged to the batch, which was further concentrated to about 300 ml under vacuum. The batch was cooled to below O0C. To the batch, Compound ll-b (5Og) and N, N diisopropylethylamine (60ml) were charged. The batch was heated to 9O0C for about 17 hours unti. the reaction was completed. The batch was concentrated under vacuum at 8O0C until no distillate came out. The batch was cooled to 20 0C. Water (255 ml) and TBME (510 ml) were added into the batch. The mixture was agitated and phases were separated in a separation funnel. The organic layer was washed again with 250 ml of water. The combined aqueous layer was back extracted with 200 ml of TBfVIE. The combined organic iayer was washed with 0.5N HCi (100 ml). The batch was concentrated at vacuum unti. 255ml TBME (510 mi) was charged info the batch and concentrated to 250 mi. After cooling to Q- <n="19"/>1O0C, a solution of 2-isopropanol hydrochloride solution (5-6N1 170ml) was added under 250C and the solution was agitated at 15-25 0C for 20 hours. TBME (255 ml) was charged into the batch and agitated at 25 0C for 2 hours. The batch was filtrated and washed with a mixture of T8ME/2-Isopropanol. (200 ml, 2/1 v/v). The wet cake was dried at vacuum oven at 50 0C to give 65.0 g (77percent) of the white solid. 1H NMR(400 MHz in CD3OD): 8.86 (S5 1 H)1 4.83(S, 2H), 3.94(m, 4H); 3.53 (m, 3H); 3.24 (t, 1 H); 2.99 (dd, 1 H); 2.66 (S5 3H)1 1.82 (m, 2H); 1.11 (m, 6H). 13C NMR (400 Mhe, CD3OD): delta 165.3; 160.4; 152.4;143.3; 139.2' 58.3; 53.8; 53.8; 51.5; 49.9, 25.1 ; 21.4; 17.1 , 10.6.

References: [1]Patent: WO2009/79490,2009,A1 .Location in patent: Page/Page column 15; 17-18.

11
[ 906559-60-2 ]
[ 77168-85-5 ]
[ 1161772-04-8 ]