Dimethylformamide dimethyl acetal → 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

HRID 13843Notes

Reaction equation

HRID 13843 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:4](=[O:31])[C:3]=1[Cl:32].CO[CH:35](OC)[N:36]([CH3:38])[CH3:37]>>[Cl:32][C:3]1[C:4](=[O:31])[N:5]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:6]2[C:11]([C:2]=1[N:1]=[CH:35][N:36]([CH3:38])[CH3:37])=[CH:10][C:9]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[C:8]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])[N:7]=2

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 112259274-amino-3-chloro-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-isobutyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 11238345n'-[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 °C

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.

Workup

  1. concentrationwas concentrated in vacuo
  2. customPurification by flash chromatography on silica
  3. washeluted with 0-30% EtOAc in hexane

Sources & evidence

ORD record
ord-44886afa73004470ad1fbce9f39604a6
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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