Trifluoroacetic acid → HCID 178514994, compound
Reaction equation
C([O:8][C:9]1[C:14]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])=[CH:13][N:12]=[C:11]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=2)[N:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[F:38][C:34]1[CH:33]=[C:32]([NH:31][C:11]2[N:10]=[C:9]([OH:8])[C:14]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][N:20]3[C:21](=[O:30])[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:28]3=[O:29])=[CH:13][N:12]=2)[CH:37]=[CH:36][CH:35]=1Participants
Procedure
To 2-(5-(4-(benzyloxy)-2-((3-fluorophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (J3, 69 mg), trifluoroacetic acid (1 mL) was added at room temperature, and the mixture was stirred overnight at the same temperature. The solvent was evaporated under reduced pressure, and then ethyl acetate and water were added to the mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid matter was washed with diisopropyl ether, and then dried under reduced pressure to obtain 2-(5-(2-((3-fluorophenyl)amino)-4-hydroxypyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (J4, 62 mg) as pale pink solid.
Workup
- customThe solvent was evaporated under reduced pressure
- additionethyl acetate and water were added to the mixture
- customThe organic layer was separated
- washwashed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- washThe obtained solid matter was washed with diisopropyl ether
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-17e59bf7126540ab822386fe378ff675
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145415B2
Reaction notes
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