Acetyl chloride → 4-(4-Acetylpiperazin-1-yl)-2-(2-difluoromethylbenzimidazol-1-yl)-6-morpholino-1,3,5-triazine
Reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[F:5][CH:6]([F:34])[C:7]1[N:11]([C:12]2[N:17]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:15]=[C:14]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:13]=2)[C:10]2[CH:30]=[CH:31][CH:32]=[CH:33][C:9]=2[N:8]=1.C1COCC1>O>[C:1]([N:27]1[CH2:26][CH2:25][N:24]([C:14]2[N:15]=[C:16]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[N:17]=[C:12]([N:11]3[C:10]4[CH:30]=[CH:31][CH:32]=[CH:33][C:9]=4[N:8]=[C:7]3[CH:6]([F:34])[F:5])[N:13]=2)[CH2:29][CH2:28]1)(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Acetyl chloride (0.14 ml, 2.0 mmol) was added dropwise to a mixture of 2-(2-difluoromethylbenzimidazol-1-yl)-4-morpholino-6-(piperazin-1-yl)-1,3,5-triazine (417 mg, 1.0 mmol) and THF (10 ml). The reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was poured into water, and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, concentrated under vacuum, and the residue was purified by silica gel column to give the target compound 4-(4-acetylpiperazin-1-yl)-2-(2-difluoromethylbenzimidazol-1-yl)-6-morpholino-1,3,5-triazine (354 mg, 7.7 mmol) in a yield of 77% as colorless crystals.
Workup
- extractionextracted with dichloromethane
- dry with materialThe extract was dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customthe residue was purified by silica gel column
Sources & evidence
- ORD record
- ord-c3092058c3bc410295ef521f85430462
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338414B2
Reaction notes
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