312736-50-8|3,5-Dichloropyrazine-2-carboxamide| Ambeed

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Quality Control of [ 312736-50-8 ] Purity: 98% SDS Specification

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Product Details of [ 312736-50-8 ]

CAS No. :	312736-50-8
Formula :	C₅H₃Cl₂N₃O
M.W :	192.00
SMILES Code :	O=C(C1=NC=C(Cl)N=C1Cl)N
MDL No. :	MFCD10000837
InChI Key :	UFKLYKVKEHHZRT-UHFFFAOYSA-N
Pubchem ID :	22665521

Safety of [ 312736-50-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 312736-50-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	40.15
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	68.87 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.1
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	0.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.88
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.	-0.39
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	1.4
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.78

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.94
Solubility	2.2 mg/ml ; 0.0114 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.	-1.94
Solubility	2.2 mg/ml ; 0.0114 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	-2.48
Solubility	0.64 mg/ml ; 0.00333 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.	-6.83 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)	2.01

Application In Synthesis of [ 312736-50-8 ]

* 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.

Upstream synthesis route of [ 312736-50-8 ]
Downstream synthetic route of [ 312736-50-8 ]

[ 312736-50-8 ] Synthesis Path-Upstream 1~2

1
[ 4774-14-5 ]
[ 77287-34-4 ]
[ 312736-50-8 ]

Yield	Reaction Conditions	Operation in experiment
36%	at 20 - 90℃; for 14 h;	To a mixture of 2,6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1,476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70percent n-hexane/EtOAc) to afford 3,5-dichloropyrazin-2-carboxamide (5.06 g, 36percent) as an oil.
36%	at 90℃;	107241 2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 °C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 °C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 °C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield). ‘HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s.,1H), 8.01 (br. s., 1H).
36%	at 90℃; for 2 h;	2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heated to 90° C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90° C. in Ig portions at 20-30 seconds intervals. An exotherm was observed and the color of the mixture turned from yellow to dark red/brown. The mixture was stirred at 90° C. for 2 h and then cooled to room temperature. The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. The aqueous layer was extracted with IPA:chloroform (1:3, 3*750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent ethyl acetate in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield).

References: [1] Organic Letters, 2013, vol. 15, # 9, p. 2156 - 2159.
[2] Patent: WO2016/6975, 2016, A2, . Location in patent: Paragraph 457-459.
[3] Patent: KR2016/7347, 2016, A, . Location in patent: Paragraph 0359; 0360; 0361; 0362.
[4] Patent: WO2018/22992, 2018, A1, . Location in patent: Paragraph 0723; 0724.
[5] Patent: US2018/72743, 2018, A1, . Location in patent: Paragraph 1328-1329.

2
[ 312736-49-5 ]
[ 312736-50-8 ]

References: [1] Patent: EP1184376, 2002, A1, . Location in patent: Page 12.

[ 312736-50-8 ] Synthesis Path-Downstream 1~30

1
[ 312736-50-8 ]
[ 108-44-1 ]
5-chloro-3-(3-methylanilino)pyrazine-2-carboxamide [ No CAS ]