4-Methyl-3-(trifluoromethyl)aniline → HCID 58168272, compound

HRID 1029199Notes

Reaction equation

HRID 1029199 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=1[C:25]([F:28])([F:27])[F:26]>>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)=[CH:20][C:19]=1[C:25]([F:26])([F:27])[F:28]

Participants

3

Reactant 2

HCID 27377154-Methyl-3-(trifluoromethyl)anilineHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168272HCID 58168272, compoundYield 17.2%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 231 using 6 (50 mg, 0.22 mmol) and 4-methyl-3-trifluoromethyl-phenylamine (0.03 mL, 0.33 mmol) to provide 236 (14 mg, 17% yield) as a brown solid. LC-MS (M+H=370, obsd.=370). 1H NMR (400 MHz, d6-DMSO): δ 11.73 (s, 1H), 9.11 (s, 1H), 8.52 (dd, 1H), 8.47 (dd, 1H), 8.18 (d, 1H), 7.90 (d, 1H), 7.54 (dd, 1H), 7.43 (m, 2H), 7.28 (m, 2H), 2.41 (s, 3).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-f5a6d0def9824edbb5b321b12836bda3
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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