Reaktion #78511

ord-3b0b20561226416d8d6b8cbe908ff7f6

Reaktionsgleichung

Cn1c(CSc2ccc(C#N)cc2)nc2cc(C(=O)O)ccc21
1-methyl-2-[(4-cyanophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid
CCOC(=O)CC[N-]CC(C)C
2-methylpropyl-N-(2-ethoxycarbonylethyl)amide
Cl
hydrochloric acid
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
CCO.CCOC(C)=O.N
ethyl acetate ethanol ammonia
→
CCOC(=O)CCN(CC(C)C)C(=O)c1ccc2c(c1)nc(CSc1ccc(C(=N)N)cc1)n2C.Cl
1-Methyl-2-[(4-amidinophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-N-(2-methylpropyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride
Ausbeute 83.0%

Edukte

Cn1c(CSc2ccc(C#N)cc2)nc2cc(C(=O)O)ccc21
1-methyl-2-[(4-cyanophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid
CCOC(=O)CC[N-]CC(C)C
2-methylpropyl-N-(2-ethoxycarbonylethyl)amide
Cl
hydrochloric acid
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
CCO.CCOC(C)=O.N
ethyl acetate ethanol ammonia
—
C25H31N6O3S

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared analogously to Example 27 from 1-methyl-2-[(4-cyanophenyl)thiomethyl]benzimidazol-5-yl-carboxylic acid-(N-(2-methylpropyl-N-(2-ethoxycarbonylethyl)amide, ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 83% of theory, C25H31N6O3S (495.65); Rf value: 0.30 (silica gel; ethyl acetate/ethanol/ammonia=50:45:5); EKA mass spectrum: (M+H)+=496.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06710055B2uspto-grants-2004_03