Potassium Carbonate → 3-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-3H-imidazole-4-carboxylic acid

HRID 900243Notes

Reaction equation

HRID 900243 reaction equation
C[O:2][C:3]([C:5]1[NH:6][CH:7]=[N:8][CH:9]=1)=[O:4].Br[CH2:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]([CH2:11][N:6]2[C:5]([C:3]([OH:2])=[O:4])=[CH:9][N:8]=[CH:7]2)=[O:13])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 565661Methyl 4-imidazolecarboxylateHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamide

Product 1

HCID 692951933-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-3H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 200 mg 3H-Imidazole-4-carboxylic acid methyl ester, 396 mg), 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide and 220 mg K2CO3 in 2 ml DMF was stirred for 16 h at RT. The solvent was removed under reduced pressure and the precipitate dissolved in 5 ml THF/water 2:1. Then, 1.5 ml KOH 10% was added at RT and the reaction mixture was stirred for 16 h. Finally, 3 ml of halfconcentrated hydrochloric acid was added to precipitate the acid as a white solid. Yield: 260 mg.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe precipitate dissolved in 5 ml THF/water 2:1
  3. additionThen, 1.5 ml KOH 10% was added at RT
  4. stirringthe reaction mixture was stirred for 16 h
  5. additionFinally, 3 ml of halfconcentrated hydrochloric acid was added
  6. customto precipitate the acid as a white solid

Sources & evidence

ORD record
ord-70ee330e5967431591b54a3791004fd3
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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