3-Methoxyphenylacetyl chloride → 1-[1-(1-Hydroxy-ethyl)-4-phenyl-butyl]-6-(3-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:26]=[C:27]([CH2:31][C:32](Cl)=O)[CH:28]=[CH:29][CH:30]=1>>[OH:19][CH:17]([CH:7]([N:6]1[C:2]2[N:1]=[C:32]([CH2:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH3:23])[CH:26]=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 400 mg (1.32 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamide and 610 mg (3.81 mmol) of 3-methoxyphenylacetyl chloride, the title compounds are prepared analogously to the protocol of Example 13. This gives 160 mg (28%) of the diastereomer which elutes more rapidly, M.p.: 92° C., and 145 mg (25%) of the diastereomer which elutes more slowly, M.p.: 54° C.
Sources & evidence
- ORD record
- ord-72d69ee13d034eafba26c5092b4d979c
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174884B1
Reaction notes
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