Reaktion #78492

ord-c718b0a3ffde408f9746283f2e89b3da

Reaktionsgleichung

CCOC(=O)CN(C(=O)c1ccc2sc(CNc3ccc(C#N)cc3)nc2c1)c1ccccn1
2-[N-(4-cyanophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
→
CCOC(=O)CN(C(=O)c1ccc2sc(CNc3ccc(C(=N)N)cc3)nc2c1)c1ccccn1.Cl.Cl
2-[N-(4-amidinophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide dihydrochloride
Ausbeute 68.0%

Edukte

CCOC(=O)CN(C(=O)c1ccc2sc(CNc3ccc(C#N)cc3)nc2c1)c1ccccn1
2-[N-(4-cyanophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
—
C25H24N6O3S

Reagenzien

CC(=O)O
acetic acid

Lösungsmittel

CCO.ClCCl
methylene chloride ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared analogously to Example 9 from 2-[N-(4-cyanophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide, ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 68% of theory, C25H24N6O3S (488.57); Rf value: 0.14 (silica gel; methylene chloride/ethanol=4:1+a few drops of acetic acid); EKA mass spectrum: (M+H)+=489.

Quelle

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