Cesium carbonate → N-(3-methyl-4-((3-(2-((4-(4-methyl-1-piperazinyl)phenyl)amino)-4-pyrimidinyl)-2-pyridinyl)oxy)phenyl)-3-(trifluoromethyl)benzamide

HRID 446324Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:47])[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=2)=[CH:31][C:30]=1[CH3:48].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH3:48][C:30]1[CH:31]=[C:32]([NH:35][C:36](=[O:47])[C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:44])([F:45])[F:46])[CH:38]=2)[CH:33]=[CH:34][C:29]=1[O:28][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To 4-(2-chloropyridin-3-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine (35 mg, 0.092 mmol), N-(4-hydroxy-3-methylphenyl)-3-(trifluoromethyl)benzamide (27 mg, 0.092 mmol) and Cs2CO3 (60 mg, 0.18 mmol) was added DMSO (0.6 mL). The mixture was heated overnight at 130° C. The crude material was purified by reverse-phase HPLC (Gilson, acidic mobile phase) to yield the title compound as a light yellow solid after aqueous workup. MS m/z=640 [M+1]+ Calc'd for C35H32F3N7O2: 639.69.

Workup

customThe crude material was purified by reverse-phase HPLC (Gilson, acidic mobile phase)

Sources & evidence

ORD record: ord-d99a882a5ba34a6d96701837ed98a8fa
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476434B2

Reaction notes

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