Trifluoroacetic acid → ((R)-3-Aminopyrrolidin-1-yl)(3-(methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indol-6-yl)methanone
Reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][S:9]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([N:22]3[CH2:26][CH2:25][C@@H:24]([NH:27]C(=O)OC(C)(C)C)[CH2:23]3)=[O:21])=[CH:17][CH:18]=2)[N:13]([C:35]2[N:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:37][N:36]=2)[CH:12]=1)=[O:10]>ClCCl>[NH2:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:20]([C:16]2[CH:15]=[C:14]3[C:19]([C:11]([S:9]([CH3:8])=[O:10])=[CH:12][N:13]3[C:35]3[N:40]=[CH:39][C:38]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[CH:37][N:36]=3)=[CH:18][CH:17]=2)=[O:21])[CH2:23]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 4M solution of TFA in dichloromethane (5.22 mL, 20.91 mmol) was added to 223d) (0.28 g, 0.52 mmol) in dichloromethane (16 mL) and the resulting mixture was stirred at room temperature for 3 h. The solution was concentrated, diluted with dichloromethane (40 mL), then washed with saturated potassium carbonate solution (2×20 mL) and dried over sodium sulfate. After evaporation of the solvent, the remnant was triturated with ether, pentane and acetone. Light yellow solid. Yield: 0.11 g (46% of theory)
Workup
- concentrationThe solution was concentrated
- additiondiluted with dichloromethane (40 mL)
- washwashed with saturated potassium carbonate solution (2×20 mL)
- dry with materialdried over sodium sulfate
- customAfter evaporation of the solvent
- customthe remnant was triturated with ether, pentane and acetone
Sources & evidence
- ORD record
- ord-b11d652a7a4348aeae1831b84fef259d
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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