1-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid → N-[(1S)-2-amino-1-[(5-amino-1H-indol-3-yl)methyl]-2-oxo-ethyl]-1-cyclohexyl-2-(3-furyl)benzimidazole-5-carboxamide
Reaction equation
[N+:1]([C:4]1[CH:18]=[C:17]2[C:7]([NH:8][CH:9]=[C:10]2[CH2:11][C@@H:12]([C:14]([NH2:16])=[O:15])[NH2:13])=[CH:6][CH:5]=1)([O-])=O.[CH:19]1([N:25]2[C:29]3[CH:30]=[CH:31][C:32]([C:34](O)=[O:35])=[CH:33][C:28]=3[N:27]=[C:26]2[C:37]2[CH:41]=[CH:40][O:39][CH:38]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[NH2:1][C:4]1[CH:18]=[C:17]2[C:7](=[CH:6][CH:5]=1)[NH:8][CH:9]=[C:10]2[CH2:11][C@H:12]([NH:13][C:34]([C:32]1[CH:31]=[CH:30][C:29]2[N:25]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:26]([C:37]3[CH:41]=[CH:40][O:39][CH:38]=3)=[N:27][C:28]=2[CH:33]=1)=[O:35])[C:14](=[O:15])[NH2:16]Participants
3
Procedure
The 5-nitrotryptophan amide derivative of example 53 was coupled to the carboxylic acid of example 2 in the usual manner. The nitro group was then reduced to the corresponding amine using SnCl2 dihydrate as described in example 48, to give the title compound of example 54 after purification by preparative C18 reversed-phase HPLC.
Sources & evidence
- ORD record
- ord-180cba272b3d4da49535c913c3b87d5d
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06794404B2
Reaction notes
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