Carbonochloridic acid, octyl ester → ethyl 3-(N-[1-methyl-2-[[4-(N-octoxycarbonylcarbamimidoyl)anilino]methyl]benzimidazole-5-carbonyl]anilino)propanoate

HRID 2288489Notes

Reaction equation

HRID 2288489 reaction equation
Cl.[C:2]1([N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26](=[NH:28])[NH2:27])=[CH:22][CH:21]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:40]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[O:41]>ClCCl.C(O)C>[C:2]1([N:8]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([CH2:18][NH:19][C:20]4[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][CH2:48][CH2:49][CH3:50])=[O:41])=[CH:22][CH:21]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 81956Carbonochloridic acid, octyl esterHCID 184125531-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylicacid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide-hydrochloride

Product 1

HCID 140409593ethyl 3-(N-[1-methyl-2-[[4-(N-octoxycarbonylcarbamimidoyl)anilino]methyl]benzimidazole-5-carbonyl]anilino)propanoateYield 34%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 90 from 1-methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide-hydrochloride and n-octyl chloroformate. Yield: 34% of theory, C37H46N6O5 (654.8) Rf value: 0.15 (silica gel; dichloromethane/ethanol=19:1) ##EQU102##

Sources & evidence

ORD record
ord-db4db05f76e741a48bfc5b0b1db44243
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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