Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylate → 3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester

HRID 896337Notes

Reaction equation

HRID 896337 reaction equation
C(N1C2C=CC=CC=2N([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:16]=3[N:15]=2)C1=O)(C)C.[CH2:31]([O:33][C:34]([N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[NH:38][C:37]1=[O:45])=[O:35])[CH3:32]>>[CH2:31]([O:33][C:34]([N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:16]=3[N:15]=2)[C:37]1=[O:45])=[O:35])[CH3:32]

Participants

3

Reactant 2

HCID 303857Ethyl 2-oxo-2,3-dihydro-1H-benzo[D]imidazole-1-carboxylateHCID 223493242-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile

Product 1

HCID 697174433-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester

Procedure

3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester was prepared by the same procedure as 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile, except using 2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester (N. Meanwell et al, J. Org. Chem, 1995, 60(6), 1565-82) and was used without purification in the next reaction.

Workup

  1. customwas used without purification in the next reaction

Sources & evidence

ORD record
ord-f163814a269b4c76b0e61c01e68240fc
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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