Reaktion #78491

ord-b17702371bd24fa3b50f9fa5a35f31ae

Reaktionsgleichung

CCOC(=O)CN(C(=O)c1ccc2sc(CCc3ccc(C#N)cc3)nc2c1)c1ccccn1
2-[2-(4-cyanophenyl)ethyl]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(CCc3ccc(C(=N)N)cc3)nc2c1)c1ccccn1.Cl.Cl
2-[2-(4-amidinophenyl)ethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide dihydrochloride
Ausbeute 95.0%

Edukte

CCOC(=O)CN(C(=O)c1ccc2sc(CCc3ccc(C#N)cc3)nc2c1)c1ccccn1
2-[2-(4-cyanophenyl)ethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide
Cl
hydrochloric acid
CCO
ethanol
O=C([O-])[O-].[NH4+].[NH4+]
ammonium carbonate
—
C26H25N5O3S

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-[2-(4-cyanophenyl)ethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(ethoxycarbonylmethyl)amide, ethanolic hydrochloric acid, ethanol, and ammonium carbonate. Yield: 95% of theory, C26H25N5O3S (487.58); Rf value: 0.20 (silica gel; methylene chloride/ethanol=4:1+a few drops of acetic acid); EKA mass spectrum: (M+H)+=488.

Quelle

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