[ CAS No. 118853-60-4 ] {[proInfo.proName]}

Name: 118853-60-4|Methyl 6-aminopyrazine-2-carboxylate|95%
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SKU: A186991
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Quality Control of [ 118853-60-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 118853-60-4 ]

SDS Specification

Alternatived Products of [ 118853-60-4 ]

Product Details of [ 118853-60-4 ]

CAS No. :	118853-60-4	MDL No. :	MFCD10697802
Formula :	C₆H₇N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MFQOPTGQOOILCR-UHFFFAOYSA-N
M.W :	153.14	Pubchem ID :	44558107
Synonyms :

Calculated chemistry of [ 118853-60-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.72
TPSA :	78.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.0
Log Po/w (XLOGP3) :	-0.84
Log Po/w (WLOGP) :	-0.15
Log Po/w (MLOGP) :	-1.03
Log Po/w (SILICOS-IT) :	0.02
Consensus Log Po/w :	-0.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.53
Solubility :	45.0 mg/ml ; 0.294 mol/l
Class :	Very soluble
Log S (Ali) :	-0.32
Solubility :	73.4 mg/ml ; 0.479 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.35
Solubility :	6.78 mg/ml ; 0.0443 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 118853-60-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 118853-60-4 ]

* 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 [ 118853-60-4 ]
Downstream synthetic route of [ 118853-60-4 ]

[ 118853-60-4 ] Synthesis Path-Upstream 1~2

1
[ 23611-75-8 ]
[ 118853-60-4 ]

Yield	Reaction Conditions	Operation in experiment
82.4%	Stage #1: With sodium azide; triphenylphosphine In dimethyl sulfoxide at 120℃; for 4 h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 120℃; for 12 h;	Methyl 6-(chloropyrazine)-2-carboxylate (13) (2g, 0.0115mmol) was dissolved in 80mL of 87 DMSO. 88 Sodium azide (3g, 0.0463mmol) and 39 triphenylphosphene (4.6g, 0.1738mmol) were added and refluxed at 120°C for 4h. 20mL of 1N 89 HCl was added and the reaction was continued at 120°C for 2h. The mixture was cooled and neutralized by aqueous NaHCO₃ solution and 131 product was extracted in ethyl acetate, dried with Na₂SO₄ which was then concentrated and dried with n-pentane to get 1.4g of compound 14 as yellow solid (yield 82.4percent). ¹H NMR (400MHz, DMSO‑d₆) δ 8.28–8.27 (m, 1H), 8.07 (s, 1H), 6.90 (s, 2H), 3.84 (s, 3H). C₆H₇N₃O₂ [M]: 153.14; MS (ESI) m/z: [M+H]⁺: 154.05

Reference： [1] European Journal of Pharmaceutical Sciences, 2018, vol. 124, p. 165 - 181

2
[ 67-56-1 ]
[ 3375-31-3 ]
[ 33332-28-4 ]
[ 118853-60-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	at 85℃; for 5 h; Large scale	A solution of 6-chloro-2-pyrazinamine (4 kg, 31 mol, 1.00 equiv), Et3N (4.7 kg,46.5 mol, 1.50 equiv), Pd(OAc)2 (139 g, 0.62mo1, 0.02 equiv), dppf (343 g, 0.62 mol, 0.02equiv) in methanol (60 L) was placed in a 100 L pressure tank reactor(10 atm).The resulting solution was allowed to react for 5 h while maintaining the temperature at 85°C. The reaction progress was monitored by TLC (DCM: MeOH = 20: 1) until the starting material was consumed completely, and cooled to room temperature. The resulting mixture was concentrated under vacuum. The residue was washed with water 50 L. Thefilter was collected and dried. The product (3.8 kg, purity = 95 percent, 80 percent yield)obtained as a pale brown solid.1H-NIVIR (300 MHz, DMSO-d6) : 8.27(1H, s), 8.06(1H, s), 6.87(2H, b), 3.84(3H, s). LC-MS: m / z = 154(M+H) +.

Reference： [1] Patent: WO2017/29602, 2017, A2, . Location in patent: Page/Page column 75; 76; 133; 134

[ 118853-60-4 ] Synthesis Path-Downstream 1~27

2
[ 118853-60-4 ]
[ 79583-19-0 ]
methyl 6-(1-methyl-1H-pyrazole-4-carboxamido)pyrazine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 25℃; for 2h;	Into a 50-mL round-bottom flask was placed pyridine (25 mL), methyl 6- aminopyrazine-2-carboxylate (1 g, 6.53 mmol, 1.00 equiv) and 1-methyl-1H-pyrazole-4- carbonyl chloride (1.13 g, 7.82 mmol, 1.20 equiv). The resulting solution was stirred for 2 h at 25 oC in an oil bath. The resulting mixture was concentrated under vacuum at 55 oC for 1 h. This resulted in 1.72 g (93% purity) of methyl 6-(1-methyl-1H-pyrazole-4-amido)pyrazine-2- carboxylate as a yellow solid.

Reference： [1]Patent: WO2016/138335,2016,A1 .Location in patent: Paragraph 00407

3
[ 67-56-1 ]
[ 3375-31-3 ]
[ 33332-28-4 ]
[ 118853-60-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; at 85℃; under 7600.51 Torr; for 5h;Large scale;	A solution of 6-chloro-2-pyrazinamine (4 kg, 31 mol, 1.00 equiv), Et3N (4.7 kg,46.5 mol, 1.50 equiv), Pd(OAc)2 (139 g, 0.62mo1, 0.02 equiv), dppf (343 g, 0.62 mol, 0.02equiv) in methanol (60 L) was placed in a 100 L pressure tank reactor(10 atm).The resulting solution was allowed to react for 5 h while maintaining the temperature at 85°C. The reaction progress was monitored by TLC (DCM: MeOH = 20: 1) until the starting material was consumed completely, and cooled to room temperature. The resulting mixture was concentrated under vacuum. The residue was washed with water 50 L. Thefilter was collected and dried. The product (3.8 kg, purity = 95 percent, 80 percent yield)obtained as a pale brown solid.1H-NIVIR (300 MHz, DMSO-d6) : 8.27(1H, s), 8.06(1H, s), 6.87(2H, b), 3.84(3H, s). LC-MS: m / z = 154(M+H) +.

Reference： [1]Patent: WO2017/29602,2017,A2 .Location in patent: Page/Page column 75; 76; 133; 134

4
[ 118853-60-4 ]
6-(((1S,3R,4S)-4-((7-fluoro-2-methoxyquinoxalin-8-yl)methylamino)-3-hydroxycyclohexylamino)methyl)-2H-pyrazino[2,3-b][1,4]oxazin-3(4H)-one [ No CAS ]