Dimethylformamide → HCID 58778009, compound

HRID 1372103Notes

Reaction equation

HRID 1372103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH2:12][CH2:13][CH3:14])[C:10]=1[Cl:11])=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)=[O:24].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]([N:25]2[CH2:26][CH2:27][N:28]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:29][CH2:30]2)=[O:24])[N:8]=[C:9]([CH2:12][CH2:13][CH3:14])[C:10]=1[Cl:11])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazineHCID 178440447HCID 178440447, compound

Product 1

HCID 58778009HCID 58778009, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 4-Chloro-5-Propyl-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=3/7) afforded the title compound as a white solid. 1H NMR (400 MHz, CDCl3): 6.94–7.0 (m, 2H), 6.82–6.90 (dd, 2H), 5.0 (s, 2H), 4.36–4.40 (q, 2H), 3.62–3.82 (m, 4H), 3.04–3.18 (m, 4H), 2.58–2.66(t, 2H), 1.64–1.76 (m, 2H), 1.34–1.38 (t, 3H), 0.94–1.0 (t, 3H). 13C NMR (400 MHz, CDCl3): 165, 160.2, 156.2, 152.4, 147, 133, 118.4, 118.2, 115.8, 115.4, 112.2, 61, 53, 50.6, 50.2, 45, 42, 30, 22.8, 14.4, 14.2.

Sources & evidence

ORD record
ord-ce2eb6fb1cfe4696a275c8e1b78b99ce
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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