Reaktion #308555

ord-f3c522404ea4472aa7ae49be4fbede58

Reaktionsgleichung

CCN(CC)CC
Triethylamine
CC(C)(C)OC(=O)N1CCC(OCC(=O)NNC(=O)c2ccncc2)CC1
4-{2-oxo-2-[N′-(pyridine-4-carbonyl)hydrazino]ethoxy}piperidine-1-carboxylic acid tert-butyl ester
→
CC(C)(C)OC(=O)N1CCC(OCc2nnc(-c3ccncc3)o2)CC1
title compound
CC(C)(C)OC(=O)N1CCC(OCc2nnc(-c3ccncc3)o2)CC1
4-(5-Pyridin-4-yl-[1,3,4]oxadiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

Edukte

CCN(CC)CC
Triethylamine
—
2-chloro-1,3-dimethyl-2-imidazolinium hexafluorophosphate
CC(C)(C)OC(=O)N1CCC(OCC(=O)NNC(=O)c2ccncc2)CC1
4-{2-oxo-2-[N′-(pyridine-4-carbonyl)hydrazino]ethoxy}piperidine-1-carboxylic acid tert-butyl ester

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethis mixture purified by flash chromatography (EtOAc)

Vorschrift

Triethylamine (149 μl, 1.06 mmol was added to stirred solution of 4-{2-oxo-2-[N′-(pyridine-4-carbonyl)hydrazino]ethoxy}piperidine-1-carboxylic acid tert-butyl ester (Preparation 16, 200 mg, 0.53 mmol) and 2-chloro-1,3-dimethyl-2-imidazolinium hexafluorophosphate (147 mg, 0.53 mmol) in CH2Cl2 (10 ml). After 18 h at rt, the solvent was reduced to a small volume and this mixture purified by flash chromatography (EtOAc), affording the title compound: RT=3.42 min; m/z (ES+)=361.1 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08207147B2uspto-grants-2012_06