Hexyl chloroformate → ethyl 3-[[2-[2-[4-(N-hexoxycarbonylcarbamimidoyl)phenyl]ethyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate

HRID 50343Notes

Reaction equation

HRID 50343 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:9]([C:11]1[CH:31]=[CH:30][C:14]2[N:15]([CH3:29])[C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:10].Cl[C:40]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:41]>ClCCl.CO>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:9]([C:11]1[CH:31]=[CH:30][C:14]2[N:15]([CH3:29])[C:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:27])[NH:28][C:40]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:41])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 22466Hexyl chloroformateHCID 18412669HCID 18412669, compound

Product 1

HCID 140409599ethyl 3-[[2-[2-[4-(N-hexoxycarbonylcarbamimidoyl)phenyl]ethyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoateYield 72%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 90 from 1-methyl-2-[2-(4-amidinophenyl)ethyl]benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride and n-hexyl chloroformate. Yield: 72% of theory, C35H42N6O5 (626.8); Rf value: 0.54 (silica gel; dichloromethane/methanol=9:1); EKA mass spectrum: (M+H)+=627; (M+Na)+=649.

Sources & evidence

ORD record
ord-27fa37c786e047c5b787eed886f0a434
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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