Trifluoroacetic acid → 2-(4-(3-(6-fluoropyridin-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetamide
Reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]([NH2:25])=[O:24])[CH:21]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]([NH2:25])=[O:24])[CH:21]=4)[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1Participants
3
Procedure
A mixture of 60 mg (0.142 mmol) of 2-(4-(3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetamide and 2 ml of trifluoroacetic acid was stirred for 18 hours. The mixture was concentrated in vacuum, the residue stirred with 5 ml of saturated aqueous sodium bicarbonate for 30 min. The precipitate was collected by filtration, washed with water and recrystallized from methanol affording 35 mg (26%) of 178 over 4 steps. ESI MS m/z 338.0 (M+1). 1H NMR (400 MHz, DMSO): 14.02 (s, 1H), 9.10 (s, 1H), 8.46 (s, 1H), 8.28 (s, 1H), 8.17-8.09 (m, 2H), 7.99 (s, 1H), 7.51 (s, 1H), 7.28 (s, 1H), 7.20 (dt, J=5.4, 2.7 Hz, 1H), 4.84 (s, 2H)
Workup
- concentrationThe mixture was concentrated in vacuum
- stirringthe residue stirred with 5 ml of saturated aqueous sodium bicarbonate for 30 min
- filtrationThe precipitate was collected by filtration
- washwashed with water
- customrecrystallized from methanol affording 35 mg (26%) of 178 over 4 steps
Sources & evidence
- ORD record
- ord-64f657e6c02b436494c7362f4eb6d7c4
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260425B2
Reaction notes
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