4-(Chloromethyl)benzoyl chloride → 4-chloromethyl-N-[4-methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]benzamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([CH:24]=1)[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:9]=1.[Cl:26][CH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>>[Cl:26][CH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([NH:7][C:8]3[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[N:11]=[C:10]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[N:9]=3)[CH:24]=2)=[O:33])=[CH:30][CH:29]=1Participants
3
Procedure
The title compound was prepared from a mixture of 4-(5-amino-2-methylanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (80 mg, 0.232 mmol) and 4-chloromethylbenzoyl chloride (53 mg, 0.278 mmol) similar to Example 139 and isolated as a yellow solid (55 mg, 48%). 1H NMR (CDCl3): 8.75 (dd, J=1.8, 4.8 Hz, 2H), 8.29 (dd, J=1.8, 4.8 Hz, 2H), 8.02 (s, 1H), 7.96 (s, 1H), 7.88 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.4 Hz, 2H), 7.37 (dd, J=1.8, 7.5 Hz, 1H), 7.32 (d, J=7.5 Hz, 1H), 7.12 (s, 1H), 6.75 (s, 1H), 4.63 (s, 2H), 2.28 (s, 3H).
Sources & evidence
- ORD record
- ord-41a6bb2b0fd747aa92f087087c3cf4c7
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06716851B2
Reaction notes
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