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

HRID 270906Notes

Reaction equation

HRID 270906 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][NH:5][C:6]=1[CH2:7][CH3:8].C([O-])([O-])=O.[K+].[K+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)=[CH:22][C:21]=1[O:35][CH3:36].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH2:33][N:5]3[C:6]([CH2:7][CH3:8])=[C:2]([Cl:1])[C:3]([C:9]([F:10])([F:12])[F:11])=[N:4]3)[CH2:28][CH2:27]2)=[CH:22][C:21]=1[O:35][CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 210709911-[4-(4-Chloro-3-methoxyphenyl)-piperazine-1-yl]-ethanoneHCID 210711484-Chloro-3-ethyl-5-(trifluoromethyl)-1H-Pyrazole

Product 1

HCID 210709881-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-(4-chloro-5-ethyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 4-Chloro-5-ethyl-3-trifluoromethyl-1-H-pyrazol, K2CO3, 1-[4-(4-Chloro-3-methoxyphenyl)-piperazine-1-yl]-ethanone and DMF. Column chromatography using a solvent mixture (hexane/ethyl acetate=2/3, Rf=0.53) afforded the title compound as white solid. 1H NMR (400 MHz, CDCl3); 7.18-7.22 (d, 2H), 6.38-6.48 (m, 2H), 4.98 (s, 2H), 3.86 (s, 3H), 3.66-3.76 (m, 4H), 3.1-3.2 (m, 4H), 2.66-2.74 (q, 2H), 1.18-1.28 (m, 3H). MS (ES) M+H) expected=464.82, found 465.

Sources & evidence

ORD record
ord-b8003260baa041d7a7f758eb0ccd1914
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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