Cyclopropanecarboxaldehyde → 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1-(1-(cyclopropylmethyl)azetidin-3-yl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one dihydrochloride
Reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:21]([C:23]3[O:24][C:25](=[O:43])[C:26]4[C:31]([C:32]=3[C:33]3[CH2:34][CH2:35][N:36]([CH:39]5[CH2:42][NH:41][CH2:40]5)[CH2:37][CH:38]=3)=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH3:22])[N:11]=[C:12]([C:13]3[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([F:20])[CH:14]=3)[C:5]=12.[CH:44]1([CH:47]=O)[CH2:46][CH2:45]1>>[ClH:1].[ClH:1].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:21]([C:23]3[O:24][C:25](=[O:43])[C:26]4[C:31]([C:32]=3[C:33]3[CH2:34][CH2:35][N:36]([CH:39]5[CH2:42][N:41]([CH2:47][CH:44]6[CH2:46][CH2:45]6)[CH2:40]5)[CH2:37][CH:38]=3)=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH3:22])[N:11]=[C:12]([C:13]3[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([F:20])[CH:14]=3)[C:5]=12Participants
3
Reactant 2
Product 1
Procedure
Title compound was prepared following the procedure described for the synthesis of Intermediate D24, from 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1-(azetidin-3-yl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one dihydrochloride (Example 156, 35 mg, 0.059 mmol) and cyclopropanecarbaldehyde (10.19 μl 0.136 mmol) to give the compound (33.8 mg, 0.050 mmol, 84% yield) as a white powder.
Sources & evidence
- ORD record
- ord-13449acd4fb3452ba06b9df9a3d21df9
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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