تفاعل #170259

ord-35f13e360d96448f9430109667183d79

معادلة التفاعل

Cl.NOCc1ccccc1
O-benzylhydroxylamine hydrochloride
CC(=O)C1CN(C(=O)/C=C/c2cnc3c(c2)CC2(CCN(C)CC2)C(=O)N3)C1
(E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1′-methyl-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one
C/C(=N\OCc1ccccc1)C1CN(C(=O)/C=C/c2cnc3c(c2)CC2(CCN(C)CC2)C(=O)N3)C1
title product
C/C(=N\OCc1ccccc1)C1CN(C(=O)/C=C/c2cnc3c(c2)CC2(CCN(C)CC2)C(=O)N3)C1
1′-Methyl-6-((E)-3-oxo-3-(3-((E)-1-(benzyloxyimino)ethyl)azetidin-1-yl)prop-1-enyl)-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزAfter concentration to dryness
  2. 2
    أخرىthe residue was purified by chromatography on silica gel

الإجراء التجريبي

O-benzylhydroxylamine hydrochloride (13.5 mg, 0.08 mmol) was added to a solution of (E)-6-(3-(3-acetylazetidin-1-yl)-3-oxoprop-1-enyl)-1′-methyl-1H-spiro[[1,8]naphthyridine-3,4′-piperidin]-2(4H)-one (23.0 mg, 0.06 mmol) in methanol (1.5 mL) at room temperature. The reaction mixture was stirred overnight. After concentration to dryness, the residue was purified by chromatography on silica gel using dichloromethane/methanol (9:1) as eluent. The title product was obtained as a pink solid (9 mg, 31%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08846711B2uspto-grants-2014_09