HCID 66588996, compound → 4-(4-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]([F:23])([F:22])[F:21])[N:17]=[CH:18][C:13]3=[C:12]([N:24]3[CH2:29][C@@H:28]4[CH2:30][C@H:25]3[CH2:26][O:27]4)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>O1CCCC1.C(OCC)(=O)C>[C@H:28]12[CH2:30][C@H:25]([N:24]([C:12]3[N:11]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=4)[N:15]=[C:14]4[N:16]([CH2:19][C:20]([F:22])([F:23])[F:21])[N:17]=[CH:18][C:13]=34)[CH2:29]1)[CH2:26][O:27]2Participants
4
Procedure
A suspension of (1S,4S)-5-(6-(4-nitrophenyl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (0.84 mmol maximum) in tetrahydrofuran (15 mL) and ethyl acetate (15 mL) was degassed by the addition of crushed dry ice and then treated with 10% palladium on carbon (50 mg). The resulting suspension was evacuated under weak vacuum and then filled with hydrogen gas (balloon). This evacuation/fill cycle was performed three more times and on the final iteration, the mixture was left to stir overnight under a hydrogen filled balloon. The mixture was filtered through a pad of diatomaceous earth, eluting with methanol. The filtrate was concentrated under reduced pressure to afford 4-(4-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline as a white foam (0.26 g, 78% over 2 steps). MS (ES+): 391.1 (M+H)+