4-(2-cyanopropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide → 4-(1-amino-2-methylpropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide
Reaction equation
[C:1]([C:3]([C:6]1[CH:30]=[CH:29][C:9]([C:10]([NH:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]3[N:25]=[C:26]([CH3:28])[CH:27]=[C:15]3[N:14]=2)=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2].[H][H]>CO.[Ni]>[NH2:2][CH2:1][C:3]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]3[N:25]=[C:26]([CH3:28])[CH:27]=[C:15]3[N:14]=2)=[O:11])=[CH:29][CH:30]=1)([CH3:4])[CH3:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
4-(2-Cyanopropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide (Compound 343 (Example 357), 75 mg, 0.19 mmol) was dissolved in methanol (5 ml). The solution was subjected to hydrogenation conditions in a flow-hydrogenator, using Raney nickel cartridge, with 30 bar of hydrogen pressure, 50° C. temperature and a flow rate of 0.5 ml/min. The reaction mixture was concentrated in vacuo to obtain the titled product 4-(1-amino-2-methylpropan-2-yl)-N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide (45 mg, 59% yield). 1H NMR (CHLOROFORM-d) δ: 8.59 (br. s., 1H), 8.07-8.20 (m, 3H), 7.91 (d, J=8.3 Hz, 2H), 7.46-7.61 (m, 5H), 6.29 (s, 1H), 2.87 (br. s., 2H), 2.50 (s, 5H), 1.36 (s, 8H), 0.87 (br. s., 3H); ESI-MS: m/z 400.4 (M+H)+.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
Sources & evidence
- ORD record
- ord-26cad5923bec454facbf9661a4f7e5ef
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921358B2
Reaction notes
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