2-(4-Methylpiperazin-1-yl)-5-(trifluoromethyl)aniline → N-(3-methyl-4-((3-(2-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)-N'-(2-(4-methyl-1-piperazinyl)-5-(trifluoromethyl)phenyl)urea

HRID 446320Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([NH:23][C:24](=O)[O:25]C2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=2)=[CH:13][CH:12]=[CH:11][N:10]=1.[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][C:41]=2[NH2:50])[CH2:36][CH2:35]1>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:23][C:24]([NH:50][C:41]2[CH:42]=[C:43]([C:46]([F:47])([F:48])[F:49])[CH:44]=[CH:45][C:40]=2[N:37]2[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]2)=[O:25])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][CH3:22])[N:16]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To phenyl 3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenylcarbamate (59 mg, 0.14 mmol) in THF (1 mL) was added 2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)benzenamine (30 mg, 0.12 mmol). The mixture was stirred for 40 hours at 80° C. The crude material was purified by silica gel chromatography (0-20% MeOH/CH2Cl2) to yield the title compound as a light yellow solid. MS m/z=593 [M+H]+. Calc'd for C30H31F3N8O2: 592.63.

Workup

customThe crude material was purified by silica gel chromatography (0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-90c95bff4fcc4c99848347b4c6fafb4d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476434B2

Reaction notes

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