Dimethylformamide → 4-Chloro-5-(5-chloro-thiophen-2-yl)-2-{2-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 1372109

Reaction equation

HRID 1372109 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:12]2[S:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:10]=1[Cl:11])=[O:5])[CH3:2].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]([F:40])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)=[O:27].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][C:26]([N:28]2[CH2:29][CH2:30][N:31]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH2:32][CH2:33]2)=[O:27])[N:8]=[C:9]([C:12]2[S:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:10]=1[Cl:11])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazineHCID 178470415HCID 178470415, compound

Product 1

HCID 587780164-Chloro-5-(5-chloro-thiophen-2-yl)-2-{2-[4-(4-fluoro-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 4-Chloro-5-(5-chloro-thiophen-2-yl)-2H-pyrazole-3-carboxylic acid ethyl ester, K2CO3, 2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone and DMF. Column chromatography using a solvent mixture (hexane/ethyl acetate=2/3) afforded the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): 7.46–7.48 (m, 1H), 6.94–7.1 (m, 2H), 6.84–6.92 (m, 3H), 5.4 (s, 2H), 4.34–4.4 (q, 2H), 3.62–3.81 (m, 4H), 3.04–3.24 (m, 4H), 1.36–1.44 (m, 3H). MS (ES) M+H) expected=511.41, found 511.

Sources & evidence

ORD record
ord-a9d57fdd323540fb85d88551d39676ff
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Linked notes

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