Reaktion #78503

ord-a30ee33bd49149a4b98c2fc5a19c4a92

Reaktionsgleichung

CCCN(CCC(=O)OCC)C(=O)c1ccc2sc(CNc3ccc(C#N)cc3)nc2c1
2-[N-(4-cyanophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
→
CCCN(CCC(=O)OCC)C(=O)c1ccc2sc(CNc3ccc(C(=N)N)cc3)nc2c1.Cl
2-[N-(4-amidinophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride
Ausbeute 83.0%

Edukte

CCCN(CCC(=O)OCC)C(=O)c1ccc2sc(CNc3ccc(C#N)cc3)nc2c1
2-[N-(4-cyanophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(n-propyl)-N-(2-ethoxycarbonylethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
—
C24H29N5O3

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-(n-propyl)-N-(2-ethoxycarbonylethyl)amide, ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 83% of theory, C24H29N5O3 (467.59); Rf value: 0.31 (silica gel; methylene chloride/ethanol=4:1+a few drops of acetic acid); EKA mass spectrum: (M+H)+=468; (2M+H)+=935.

Quelle

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