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

HRID 623017Notes

Reaction equation

HRID 623017 reaction equation
[Br: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.[CH2:33]([N:35]1[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36]1)[CH3:34]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:40][CH:37]3[CH2:38][CH2:39][N:35]([CH2:33][CH3:34])[CH2:36]3)=[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 128619421-Ethylpyrrolidin-3-amineHCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143902772-(4-Bromophenyl)-N-(1-ethyl-3-pyrrolidinyl)-3H-imidazo[4,5-b]pyridine-3-acetamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0151 mole), 1,1'-carbonyldiimidazole (2.45 g, 0.0151 mole), and anhydrous tetrahydrofuran (100 ml) was stirred at room temperature with a stream of nitrogen bubbling through it for 3 hours. The nitrogen flow was stopped and a solution of 1-ethyl-3-aminopyrrolidine (1.89 g, 0.0166 mole) in dry tetrahydrofuran (25 ml) was added. The solution was stirred at room temperature under nitrogen for 2 hours. The reaction mixture was concentrated in vacuo and the residue triturated in water (100 ml) and filtered. The filter cake was recrystallized from isopropyl alcohol-isopropyl ether to give 4.64 g (72%) of white needles, mp 202.5°-204° C.

Workup

  1. stirringThe solution was stirred at room temperature under nitrogen for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue triturated in water (100 ml)
  4. filtrationfiltered
  5. customThe filter cake was recrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-deac4f7735f54f1da9bea6e40d0f025c
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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