1,1'-Carbonyldiimidazole → 2-(4-Chlorophenyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride

HRID 2351658

Reaction equation

HRID 2351658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:33][CH2:34][CH:35]1[CH2:39][CH2:38][CH2:37][N:36]1[CH2:40][CH3:41]>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:33][CH2:34][CH:35]3[CH2:39][CH2:38][CH2:37][N:36]3[CH2:40][CH3:41])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 212914172-(4-Chlorophenyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3H-imidazo[4,5-b]pyridine-3-acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid 5.0 g (0.0174 mole) and 1,1'-carbonyldiimidazole (2.82 g, 0.0174 mole) in 150 ml of tetrahydrofuran was stirred at room temperature for 3 hrs with a stream of nitrogen bubbling through it. The 2-(aminomethyl)-1-ethylpyrrolidine (4.46 g, 0.0348 mole) was added dropwise and the reaction mixture was allowed to stir at room temperature overnight.

Workup

  1. stirringto stir at room temperature overnight

Sources & evidence

ORD record
ord-4e9cbb4125f44d7c86147f1241fd8b3b
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Linked notes

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