1,1'-Carbonyldiimidazole → HCID 23037390, compound

HRID 2073012Notes

Reaction equation

HRID 2073012 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-c4a5ccba73fd49d59e0f5b3270e53d6b
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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