Reaction #42121

ord-44886afa73004470ad1fbce9f39604a6

Reaction equation

CC(C)Cn1c(=O)c(Cl)c(N)c2cc(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3Cl)nc21
product
CC(C)Cn1c(=O)c(Cl)c(N)c2cc(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3Cl)nc21
4-amino-3-chloro-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-1,8-naphthyridin-2(1H)-one
COC(OC)N(C)C
N,N-dimethylformamide dimethylacetal
CC(C)Cn1c(=O)c(Cl)c(N=CN(C)C)c2cc(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3Cl)nc21
title compound
CC(C)Cn1c(=O)c(Cl)c(N=CN(C)C)c2cc(-c3ccc(Cl)cc3)c(-c3ccc(Cl)cc3Cl)nc21
N′-[3-chloro-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N,N-dimethylimidoformamide

Conditions

Temperature
95°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationwas concentrated in vacuo
  2. 2
    OtherPurification by flash chromatography on silica
  3. 3
    Washeluted with 0-30% EtOAc in hexane

Procedure

The product of EXAMPLE 61 (50 mg) was combined with N,N-dimethylformamide dimethylacetal (4 mL). The reaction was heated to 95° C. and stirred for 90 minutes at which the solution was concentrated in vacuo. Purification by flash chromatography on silica eluted with 0-30% EtOAc in hexane afforded the title compound (E/Z mixture of isomers). HPLC/MS: 560.9 (M+1), 562.9 (M+3); Rt=4.48 min.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728141B2uspto-grants-2010_06