Dimethylformamide → 1-[4-(4-Chloro-3-methoxyphenyl)-piperazin-1-yl]-2-(4-chloro-5-[3-Fluoro-phenyl]-3-trifluoromethyl-pyrazol-1-yl)-ethanone

HRID 270913Notes

Reaction equation

HRID 270913 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([F:17])([F:16])[F:15])=[N:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([O:41][CH3:42])[CH:35]=2)[CH2:30][CH2:29]1)=[O:27].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([N:31]2[CH2:32][CH2:33][N:28]([C:26](=[O:27])[CH2:25][N:5]3[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=4)=[C:2]([Cl:1])[C:3]([C:14]([F:15])([F:17])[F:16])=[N:4]3)[CH2:29][CH2:30]2)=[CH:35][C:36]=1[O:41][CH3:42]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanoneHCID 178505660HCID 178505660, compound

Product 1

HCID 210709871-[4-(4-Chloro-3-methoxyphenyl)-piperazin-1-yl]-2-(4-chloro-5-[3-Fluoro-phenyl]-3-trifluoromethyl-pyrazol-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 4-Chloro-5-[3-Fluorophenyl]-3-trifluoromethyl-1H-pyrazole, K2CO3, 2-Chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone and DMF. Column chromatography using a solvent mixture (hexane/ethyl acetate=2/3, Rf=0.59) afforded the title compound as a white solid. 1H NMR (400 MHz, CDCl3): 7.64-7.68 (d, 1H), 7.56-7.62 (d, 1H), 7.36-7.42 (m, 1H), 7.22-7.24 (m, 2H), 7.08-7.12 (m, 1H), 6.42-6.52 (m, 2H), 5.2 (s, 2H), 3.9 (s, 3H), 3.62-3.82 (m, 4H), 3.12-3.22 (m, 4H).

Sources & evidence

ORD record
ord-1c927c9562ff4949be1444ac8ecf3e6e
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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