4-Methoxyphenylacetyl chloride → 1-[1-(1-Hydroxy-ethyl)-4-phenyl-butyl]-6-(4-methoxy-benzyl)-1,5-dihydro-pyrazolo-[3,4-d]pyrimidin-4-one
Reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:20]([NH2:22])=[O:21].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](Cl)=O)=[CH:27][CH:26]=1>>[OH:19][CH:17]([CH:7]([N:6]1[C:2]2[N:1]=[C:32]([CH2:31][C:28]3[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[NH:22][C:20](=[O:21])[C:3]=2[CH:4]=[N:5]1)[CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:18]Participants
3
Procedure
Starting from 1 g (3.31 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamide and 1.52 g (8.26 mmol) of 4-methoxyphenylacetyl chloride, the title compounds are prepared analogously to the protocol of Example 13. This gives 240 mg (17%) of the diastereomer which elutes more rapidly, M.p.: 41° C., and 134 mg (9%) of the diastereomer which elutes more slowly, M.p.: 48° C.
Sources & evidence
- ORD record
- ord-0e0ac07c20f94b93890f7145b086b8e8
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174884B1
Reaction notes
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