5-amino-1-methyl-1H-imidazole-4-carbonitrile → 7-Methoxy-2-methoxymethylbenzofuran-4-carboxylic acid (5-cyano-3-methyl-3H-imidazol-4-yl)-amide

HRID 2270123Notes

Reaction equation

HRID 2270123 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:25][CH3:26])=[C:17]3[O:21][C:20]([CH2:22][O:23][CH3:24])=[CH:19][C:18]=23)=[O:12])=CC=1)([O-])=O.[NH2:27][C:28]1[N:32]([CH3:33])[CH:31]=[N:30][C:29]=1[C:34]#[N:35]>O>[C:34]([C:29]1[N:30]=[CH:31][N:32]([CH3:33])[C:28]=1[NH:27][C:11]([C:13]1[CH:14]=[CH:15][C:16]([O:25][CH3:26])=[C:17]2[O:21][C:20]([CH2:22][O:23][CH3:24])=[CH:19][C:18]=12)=[O:12])#[N:35]

Participants

4

Reactant 2

HCID 110516355-amino-1-methyl-1H-imidazole-4-carbonitrileHCID 698380087-Methoxy-2-methoxymethylbenzofuran-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 102910017-Methoxy-2-methoxymethylbenzofuran-4-carboxylic acid (5-cyano-3-methyl-3H-imidazol-4-yl)-amideYield 74.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared from 7-methoxy-2-methoxymethylbenzofuran-4-carboxylic acid 4-nitro-phenyl ester (250 mg) and 5-amino-1-methyl-1-H-imidazole-4-carbonitrile (171 mg). The reaction was stirrred for 1 hour and 40 minutes. Water (1 ml) was added and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 10% methanol in dichloromethane afforded the title compound as a pale yellow solid (178 mg).

Workup

  1. customthe solvent removed in vacuo
  2. customPurification by column chromatography on silica eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-e86141202ea64ac1b453ce12c9b51f70
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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