Dimethylamine → 1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-N,N-dimethyl-3-(methylsulfinyl)-1H-indole-6-carboxamide
Reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:3].F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CNC.[F:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1[CH:45]=[N:46][C:47]([N:50]2[C:58]3[C:53](=[CH:54][CH:55]=[C:56]([C:59](O)=[O:60])[CH:57]=3)[C:52]([S:62]([CH3:64])=[O:63])=[CH:51]2)=[N:48][CH:49]=1>ClCCl>[F:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1[CH:49]=[N:48][C:47]([N:50]2[C:58]3[C:53](=[CH:54][CH:55]=[C:56]([C:59]([N:2]([CH3:3])[CH3:1])=[O:60])[CH:57]=3)[C:52]([S:62]([CH3:64])=[O:63])=[CH:51]2)=[N:46][CH:45]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
HATU (158 mg, 0.41 mmol), diisopropylethylamine (0.32 ml, 0.41 mmol) and dimethylamine (2M in THF) (0.95 mL, 1.89 mmol) were added to an ice-cooled suspension of 51e) (150 mg, 0.38 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with dichloromethane (40 mL) and washed with saturated ammonium chloride solution (2×30 mL), saturated sodium hydrogen carbonate solution (2×30 mL), water (30 mL), and brine (30 mL). The organic phase was dried over sodium sulfate and evaporated. The remnant was purified by column chromatography [100-200 mesh silica; 2% methanol in dichloromethane]. White solid. Yield: 62 mg (38% of theory). LC-MS (method 5): Rt=2.99 min; m/z [M+H]+=423.2
Workup
- temperaturecooled
- washwashed with saturated ammonium chloride solution (2×30 mL), saturated sodium hydrogen carbonate solution (2×30 mL), water (30 mL), and brine (30 mL)
- dry with materialThe organic phase was dried over sodium sulfate
- customevaporated
- customThe remnant was purified by column chromatography [100-200 mesh silica; 2% methanol in dichloromethane]
Sources & evidence
- ORD record
- ord-852966e3be5e4e229c4a3ebfc2defb1e
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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