Hydrochloric Acid → 3-Methyl-2-[2-(4-amidinophenyl)ethyl]-imidazo[4,5-b]pyridin-6-yl-carboxylic acid-n-(2-pyridyl)-n-(2-methoxycarbonylethyl)-amide-hydrochloride

HRID 50194Notes

Reaction equation

HRID 50194 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:8]([C:10]1[CH:11]=[C:12]2[N:18]=[C:17]([CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[N:16]([CH3:29])[C:13]2=[N:14][CH:15]=1)=[O:9].[ClH:36].C(=O)([O-])[O-].[NH4+:41].[NH4+].C(OCC)(=O)C.C(O)C.N>CO>[ClH:36].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:8]([C:10]1[CH:11]=[C:12]2[N:18]=[C:17]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27](=[NH:41])[NH2:28])=[CH:25][CH:26]=3)[N:16]([CH3:29])[C:13]2=[N:14][CH:15]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 184123843-methyl-2-[2-(4-cyanophenyl)ethyl]-imidazo[4,5-b]pyridin-6-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)-amideHCID 86587043Ethyl acetate ethanol ammonia

Product 1

HCID 184126153-Methyl-2-[2-(4-amidinophenyl)ethyl]-imidazo[4,5-b]pyridin-6-yl-carboxylic acid-n-(2-pyridyl)-n-(2-methoxycarbonylethyl)-amide-hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared analogously to Example 1 from 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[4,5-b]pyridin-6-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide, methanolic hydrochloric acid, methanol, and ammonium carbonate. Yield: 75% of theory, C26H27N7O3 (485.55); Rf value: 0.31 (silica gel; ethyl acetate/ethanol/ammonia=50:45:5); EKA mass spectrum: (M+H)+=486.

Sources & evidence

ORD record
ord-ea973c5662ba41b396462a541c2758e8
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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