2-(3,4-Dichlorophenyl)acetyl chloride → HCID 131722270, compound

HRID 566336Notes

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]=[C:4]([CH3:20])[C:3]=1[C:21]([NH2:23])=[O:22].[Cl:24][C:25]1[CH:26]=[C:27]([CH2:32]C(Cl)=O)[CH:28]=[CH:29][C:30]=1[Cl:31].[CH2:36]1CCCCC1.C(OCC)(=O)C>>[Cl:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:32][N:23]1[C:21](=[O:22])[C:3]2[C:4]([CH3:20])=[N:5][N:6]([CH:7]([CH:17]([OH:19])[CH3:18])[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:2]=2[N:1]=[CH:36]1

Participants

Reactant 3

HCID 27581492-(3,4-Dichlorophenyl)acetyl chloride

HCID 21266062HCID 21266062, compound

HCID 21867204Cyclohexane ethylacetate

Product 1

HCID 131722270HCID 131722270, compound

Procedure

Starting from 805 mg (2.55 mmol) of 5-amino-1-[1-(1-hydroxy-ethyl)-4-phenyl-butyl]-3-methyl-1H-pyrazole-4-carboxamide and 1.41 g (6.59 mmol) of 3,4-dichlorophenylacetyl chloride, are employed analogously to the protocol of Example 32 and 33. This gives 217 mg (18%) of the diastereomer which elutes more rapidly, Rf=0.2 (cyclohexane/ethyl acetate=2:1) and 186 mg (15%) of the diastereomer which elutes more slowly, M.p.: 160° C.

Sources & evidence

ORD record: ord-22841afbd8c34df888750d0dfcaf013b
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174884B1

Reaction notes

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