[ CAS No. 77862-95-4 ]

Name: 77862-95-4|Methyl 1H-imidazo[4,5-b]pyridine-6-carboxylate|98%
Brand: Ambeed
SKU: A242751
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Quality Control of [ 77862-95-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 77862-95-4 ]

SDS Specification

Alternatived Products of [ 77862-95-4 ]

Product Details of [ 77862-95-4 ]

CAS No. :	77862-95-4	MDL No. :	MFCD13176754
Formula :	C₈H₇N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UBEWQOSTWIOOIX-UHFFFAOYSA-N
M.W :	177.16	Pubchem ID :	71433321
Synonyms :

Calculated chemistry of [ 77862-95-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.17
TPSA :	67.87 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.96
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	0.74
Log Po/w (MLOGP) :	0.16
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	0.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.7
Solubility :	3.56 mg/ml ; 0.0201 mol/l
Class :	Very soluble
Log S (Ali) :	-1.6
Solubility :	4.46 mg/ml ; 0.0252 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.61
Solubility :	0.433 mg/ml ; 0.00244 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 77862-95-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 77862-95-4 ]

* 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 [ 77862-95-4 ]
Downstream synthetic route of [ 77862-95-4 ]

[ 77862-95-4 ] Synthesis Path-Upstream 1~3

1
[ 64-18-6 ]
[ 104685-76-9 ]
[ 77862-95-4 ]

Yield	Reaction Conditions	Operation in experiment
1138 mg	at 90℃; for 2.5 h;	Step 2: A stirred mixture of methyl 5,6-diaminonicotinate (1.69 g, 10.12 mmol) from Step 1 of this Example,formic acid (0.5 mL), and triethylorthoformate (25 mL) was heated at 90 °C for 2.5 h. The reaction mixture was cooledto rt and then the precipitated solid was collected by filtration and dried to afford methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate (588 mg, 33percent) as a cream solid which did not require further purification. The filtrate was concentratedunder reduced pressure, and the residue purified by silica gel flash chromatography eluting with 100percent DCM to 10percentMeOH in DCM to afford additional methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate (550 mg, 31percent) as a cream solid. 1HNMR (300 MHz, DMSO-d6) δ 13.33 (br s, 1H), 8.95 (d, J = 1.5 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J = 1.5 Hz, 1H), 3.91 (s,3H). LCMS (ESI) m/z 178 (M+H)+.

Reference： [1] Patent: EP2766359, 2016, B1, . Location in patent: Paragraph 0585

2
[ 122-51-0 ]
[ 104685-76-9 ]
[ 77862-95-4 ]

Reference： [1] Patent: US2002/193398, 2002, A1,
[2] Patent: US6610692, 2003, B1,

3
[ 104685-75-8 ]
[ 77862-95-4 ]

Reference： [1] Patent: EP2766359, 2016, B1,

[ 77862-95-4 ] Synthesis Path-Downstream 1~11

1
[ 122-51-0 ]
[ 104685-76-9 ]
[ 77862-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid;	Step C Methyl-7-azabenzimidazole-5-carboxylate A mixture of methyl-5,6-diaminonicotinate (461 mg, 2.76 mmol), formic acid (250 muL) and triethyl orthoformate (7.5 mL) was heated to 100 C. for 2 h. The mixture was then concentrated to an oily solid. Silica gel chromatography (8:1:1 EtOAc-MeOH-NH4OH) afforded the title compound as a cream-colored solid: Rf (8:1:1 EtOAc-MeOH-NH4OH)=0.22; 1H NMR (400 MHz, DMSO-d6): delta8.94 (d, J=2.0 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J=2.0 Hz, 1H), 3.91 (s, 3H).
	With formic acid;	Step C Methyl-7-azabenzimidazole-5-carboxylate A mixture of methyl-5,6-diaminonicotinate (461 mg, 2.76 mmol), formic acid (250 muL) and triethyl orthoformate (7.5 mL) was heated to 100 C. for 2 h. The mixture was then concentrated to an oily solid. Silica gel chromatography (8:1:1 EtOAc-MeOH-NH4OH) afforded the title compound as a cream-colored solid: Rf(8:1:1 EtOAc-MeOH-NH4OH)=0.22; 1H NMR (400 MHz, DMSO-d6): delta 8.94 (d, J=2.0 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J=2.0 Hz, 1H), 3.91 (s, 3H).

Reference： [1]Patent: US2002/193398,2002,A1
[2]Patent: US6610692,2003,B1

2
[ 64-18-6 ]
[ 104685-76-9 ]
[ 77862-95-4 ]

Yield	Reaction Conditions	Operation in experiment
1138 mg	With orthoformic acid triethyl ester; at 90℃; for 2.5h;	Step 2: A stirred mixture of methyl 5,6-diaminonicotinate (1.69 g, 10.12 mmol) from Step 1 of this Example,formic acid (0.5 mL), and triethylorthoformate (25 mL) was heated at 90 C for 2.5 h. The reaction mixture was cooledto rt and then the precipitated solid was collected by filtration and dried to afford methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate (588 mg, 33%) as a cream solid which did not require further purification. The filtrate was concentratedunder reduced pressure, and the residue purified by silica gel flash chromatography eluting with 100% DCM to 10%MeOH in DCM to afford additional methyl 3H-imidazo[4,5-b]pyridine-6-carboxylate (550 mg, 31%) as a cream solid. 1HNMR (300 MHz, DMSO-d6) delta 13.33 (br s, 1H), 8.95 (d, J = 1.5 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J = 1.5 Hz, 1H), 3.91 (s,3H). LCMS (ESI) m/z 178 (M+H)+.

Reference： [1]Patent: EP2766359,2016,B1 .Location in patent: Paragraph 0585

3
[ 77862-95-4 ]
methyl3-((2-(methylsulfinyl)benzo[d]thiazol-6-yl)methyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate [ No CAS ]
methyl 3-((2-(methylsulfonyl)benzo[d]thiazol-6-yl)methyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate [ No CAS ]