4-(3-(Bromomethyl)-2,5-difluorophenyl)morpholin-3-one → 4-(2,5-Difluoro-3-((6-((1-methyl-1H-pyrazol-4-yl)amino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)morpholin-3-one
Reaction equation
Br[CH2:2][C:3]1[C:4]([F:17])=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C:11]2=[O:16])[CH:6]=[C:7]([F:9])[CH:8]=1.[CH3:18][N:19]1[CH:23]=[C:22]([NH:24][C:25]2[N:30]=[C:29]3[NH:31][N:32]=[CH:33][C:28]3=[CH:27][N:26]=2)[CH:21]=[N:20]1>>[F:17][C:4]1[C:3]([CH2:2][N:31]2[C:29]3=[N:30][C:25]([NH:24][C:22]4[CH:21]=[N:20][N:19]([CH3:18])[CH:23]=4)=[N:26][CH:27]=[C:28]3[CH:33]=[N:32]2)=[CH:8][C:7]([F:9])=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][C:11]1=[O:16]Participants
3
Procedure
The title compound was prepared as in Example 1 (Step ii) using 4-(3-(bromomethyl)-2,5-difluorophenyl)morpholin-3-one and N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine. 1H NMR (d6-DMSO) δ 9.90 (s, 1H), 8.93 (s, 1H), 8.13-8.05 (m, 2H), 7.56 (s, 1H), 7.48-7.42 (m, 1H), 7.14 (s, 1H), 5.63 (s, 2H), 4.23 (s, 2H), 3.99-3.93 (m, 2H), 3.83 (s, 3H), 3.70-3.63 (m, 2H); LC-MS method B, (ES+) 441, RT=6.82 min.
Sources & evidence
- ORD record
- ord-56caad555c584f61b68a72ae34e4c891
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242987B2
Reaction notes
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