Réaction #78577

ord-02468be8aaef47d6928b4d949e40a941

Équation de réaction

CCOC(=O)CCN(C(=O)c1ccc2c(c1)nc(CNc1ccc(C(=N)N)cc1)n2C)c1ccccc1.Cl
1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride
CS(=O)(=O)CCOC(=O)Cl
2-(methylsulfonyl)ethyl chloroformate
→
CCOC(=O)CCN(C(=O)c1ccc2c(c1)nc(CNc1ccc(C(=N)NC(=O)OCCS(C)(=O)=O)cc1)n2C)c1ccccc1
1-Methyl-2-[N-[4-[N-(2-(methylsulfonyl)ethyloxycarbonyl]amidino]phenyl]aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide
Rendement 66.0%

Réactifs

CCOC(=O)CCN(C(=O)c1ccc2c(c1)nc(CNc1ccc(C(=N)N)cc1)n2C)c1ccccc1.Cl
1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride
CS(=O)(=O)CCOC(=O)Cl
2-(methylsulfonyl)ethyl chloroformate
—
C32H36N6O7S

Réactifs

Aucun

Solvants

CCO.ClCCl
dichloromethane ethanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

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 2-(methylsulfonyl)ethyl chloroformate. Yield: 66% of theory, C32H36N6O7S (648.8); Rf value: 0.44 (silica gel; dichloromethane/ethanol=19:1); EKA mass spectrum: (M+H)+=649; (M+H+Na)++=336(M+2H)++=325.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06710055B2uspto-grants-2004_03