N-(4-Aminophenyl)-4-fluoro-2-trifluoromethyl-benzamide → 4-Fluoro-N-[4-(9-trifluoromethyl-6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-ylamino)-phenyl]-2-trifluoromethyl-benzamide

HRID 1029263Notes

Reaction equation

HRID 1029263 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:41])[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[C:37]([F:40])([F:39])[F:38])=[CH:24][CH:23]=1>>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:29]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:2]3[CH:11]=[CH:10][N:9]=[C:8]4[C:3]=3[C:4]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:5]=3[C:6](=[O:12])[NH:7]4)=[CH:27][CH:26]=2)=[O:41])=[C:31]([C:37]([F:38])([F:39])[F:40])[CH:32]=1

Participants

3

Reactant 2

HCID 44603462N-(4-Aminophenyl)-4-fluoro-2-trifluoromethyl-benzamideHCID 686488171-chloro-9-trifluoromethyl-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 581683234-Fluoro-N-[4-(9-trifluoromethyl-6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-ylamino)-phenyl]-2-trifluoromethyl-benzamide

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 378, method 2 using 1-chloro-9-trifluoromethyl-5H-benzo[c][1,8]naphthyridin-6-one and N-(4-amino-phenyl)-4-fluoro-2-trifluoromethyl-benzamide to provide 404. LC-MS (M+H=561, obsd.=561). 1H NMR (400 MHz, DMSO-d6): δ, 6.96 (d, 1H), 7.18 (d, 2H), 7.54 (m, 2H), 7.76 (m, 2H), 7.78 (d, 1H), 7.97 (d, 1H), 8.10 (d, 1H), 8.27 (s, 1H), 8.99 (s, 1H), 10.25 (s, 1H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-5eb05de46acf4cacb382d0a135b19dbc
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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