Dimethylformamide → HCID 58778043, compound

HRID 1372115Notes

Reaction equation

HRID 1372115 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:12])=[N:8][NH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)=[O:22].CN(C=O)C>CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:12])=[N:8][N:9]([CH2:20][C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[O:22])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 683559ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylateHCID 18485111-(Chloroacetyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 58778043HCID 58778043, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Protocol T was followed using 3-Amino-5-methyl-1H-pyrazole-4-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=1/4) afforded the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): 6.94–7.1 (m, 2H), 6.84–6.88 (m, 2H), 5.52 (s, 2H), 4.78 (s, 2H), 4.24–4.32 (q, 2H), 3.74–3.82 (m, 4H), 3.0–3.1 (m, 4H), 2.3 (s, 3H), 1.31–1.38 (t, 3H). MS (ES) M+H expected 389.43, found 390.1.

Sources & evidence

ORD record
ord-ad957a5f3fd4425eaf7b4121c56e65d2
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

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