2-Nitroaniline → 3-(3,5-dimethoxyphenyl)-1,8-dimethyl-7-(2-nitrophenylamino)-1,6-naphthyridin-2(1H)-one

HRID 2404051Notes

Reaction equation

Cl[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)[C:8](=[O:14])[N:9]2[CH3:13])=[CH:4][N:3]=1.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH2:34])([O-:27])=[O:26].C([O-])(C)(C)C.[K+]>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([C:7]2[C:8](=[O:14])[N:9]([CH3:13])[C:10]3[C:5]([CH:6]=2)=[CH:4][N:3]=[C:2]([NH:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N+:25]([O-:27])=[O:26])[C:11]=3[CH3:12])[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-chloro-3-(3,5-dimethoxyphenyl)-1,8-dimethyl-1,6-naphthyridin-2(1H)-one (800 mg, 2.32 mmol), 2-nitrobenzenamine (320 mg, 2.32 mmol), Pd2(dba)3 (100 mg), John-Phos (100 mg) and potassium tert-butanolate (480 mg, 4.64 mmol) in N,N-dimethylformamide (10 mL) was heated in sealed tube at 100° C. under microwave for 1 h. LCMS monitored the reaction was completed. The mixture was concentrated and purified by Prep-HPLC to get the title compound (150 mg, 15%) as a brown solid. MS (ES+) C24H22N4O5 requires: 446. found: 447 [M+H]+.

Workup

concentrationThe mixture was concentrated
custompurified by Prep-HPLC

Sources & evidence

ORD record: ord-a364348cd73e460787fed6b192680864
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802697B2

Reaction notes

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