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

HRID 1372124Notes

Reaction equation

HRID 1372124 reaction equation
[Cl:1][C:2]1[C:3]([CH:11]([CH3:13])[CH3:12])=[N:4][NH:5][C:6]=1[C:7]([F:10])([F:9])[F:8].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][N:30]([C:33](=[O:35])[CH3:34])[CH2:29][CH2:28]2)=[CH:23][C:22]=1[O:36][CH3:37].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH:11]([CH3:13])[CH3:12])=[N:4][N:5]([CH2:34][C:33]([N:30]2[CH2:29][CH2:28][N:27]([C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([O:36][CH3:37])[CH:23]=3)[CH2:32][CH2:31]2)=[O:35])[C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 210709911-[4-(4-Chloro-3-methoxyphenyl)-piperazine-1-yl]-ethanoneHCID 178440440HCID 178440440, compound

Product 1

HCID 210710582-(4-Chloro-3-isopropyl-5-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 4-Chloro-3-isopropyl-5-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=0.45) afforded the title compound as white solid. 1H NMR (400 MHz, CDCl3); 7.19–7.22 (d, 2H), 6.38–6.48 (m, 2H), 5 (s, 2H), 3.86 (s, 3H), 3.62–3.78 (m, 4H), 3.08–3.18 (m, 4H), 2.98–3.04 (m, 1H), 1.35–1.41 (d, 6H). 13C NMR (400 MHz, CDCl3): 163.8, 154.8, 150.5, 130, 109.8, 102, 56.4, 52.8, 50, 49.8, 45.2, 42.6, 26.8, 20.

Sources & evidence

ORD record
ord-2e53686edf70407db7707044ad37941f
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

Loading…