4-Chlorophenylacetyl chloride → 6-(4-Chloro-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1,5-dihydro-pyrazolo-[3,4-d]pyrimidin-4-one

HRID 566332Notes

Reaction equation

HRID 566332 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].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](Cl)=O)=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[NH:22][C:20](=[O:21])[C:3]3[CH:4]=[N:5][N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:2]=3[N:1]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 906924-Chlorophenylacetyl chlorideHCID 212660785-Amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamide

Product 1

HCID 1357028726-(4-Chloro-benzyl)-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1,5-dihydro-pyrazolo-[3,4-d]pyrimidin-4-one

Procedure

Starting from 400 mg (1.32 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-1H-pyrazole-4-carboxamide and 626 mg (3.77 mmol) of 4-chlorophenylacetyl chloride, the title compounds are prepared analogously to the protocol of Example 13. This gives 150 mg (26%) of the diastereomer which elutes more rapidly, M.p.: 125° C., and 90 mg (16%) of the diastereomer which elutes more slowly, M.p.: 101° C.

Sources & evidence

ORD record
ord-19fe609b4c7a492b93769cc4a424caed
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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