1,1'-Carbonyldiimidazole → HCID 23037390, compound

HRID 1709493Notes

Reaction equation

HRID 1709493 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=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>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 128619421-Ethylpyrrolidin-3-amineHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 23037390HCID 23037390, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'-carbonyldiimidazole (2.82 g, 0.0174 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 (2.18 g, 0.0192 mole) in dry tetrahydrofuran (25 ml) was added. The solution was stirred at room temperature under nitrogen for 1 hour. The reaction mixture was concentrated in vacuo and the residue triturated in potassium bicarbonate solution (75 ml) and filtered. The filter cake was washed with water and recrystallized from isopropyl alcohol-isopropyl ether to give 2.25 g (28%) of beige solid, mp 154°-157° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue triturated in potassium bicarbonate solution (75 ml)
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customrecrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-f76ef8016b51429fb145771cc45c033f
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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