Dimethylformamide → 1-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-(3-heptafluoropropyl-5-methyl-4-nitro-pyrazol-1-yl)-ethanone

HRID 270859Notes

Reaction equation

HRID 270859 reaction equation
[F:1][C:2]([F:19])([C:15]([F:18])([F:17])[F:16])[C:3]([F:14])([F:13])[C:4]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([CH3:12])[NH:6][N:5]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)=[O:29].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[F:42][C:39]1[CH:38]=[CH:37][C:36]([N:33]2[CH2:32][CH2:31][N:30]([C:28](=[O:29])[CH2:27][N:6]3[C:7]([CH3:12])=[C:8]([N+:9]([O-:11])=[O:10])[C:4]([C:3]([F:13])([F:14])[C:2]([F:1])([F:19])[C:15]([F:17])([F:18])[F:16])=[N:5]3)[CH2:35][CH2:34]2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazineHCID 27749443-(Heptafluoropropyl)-5-methyl-4-nitro-1H-pyrazole

Product 1

HCID 210710011-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-2-(3-heptafluoropropyl-5-methyl-4-nitro-pyrazol-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 3-Heptafluoropropyl-5-methyl-4-nitro-1H-pyrazole, K2CO3, 2-Chloro-1-[4-(4-fluoro-phenyl)-piperazin-1-yl]-ethanone and DMF. Column chromatography using a solvent mixture (hexane/ethyl acetate=3/7) afforded the title compound as oil. 1H NMR (400 MHz, CDCl3): 6.9-7.0 (m, 2H), 6.8-6.9 (m, 2H), 5.06-5.14 (d, 2H), 3.6-3.8 (m, 4H), 3.06-3.18 (m, 4H), 2.56-2.66 (d, 3H). 13C NMR (400 MHz, CDCl3): 160, 146.2, 144, 119.2, 118, 52.2, 50.8, 50.4, 46, 42.2, 12.

Sources & evidence

ORD record
ord-c5d287ebb6fb4e39a962a58fb615b619
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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