Sodium Carbonate → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramide

HRID 1927592Notes

Reaction equation

HRID 1927592 reaction equation
[CH2:1]([CH:3]([CH2:20][CH3:21])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:9]([F:19])[CH:8]=1)=[O:5])[CH3:2].Br[CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[NH3:6].[CH2:29]([N:26]([CH2:27][CH3:28])[C:24]([CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[CH:3]([CH2:1][CH3:2])[CH2:20][CH3:21])=[CH:8][C:9]=2[F:19])[CH2:18][CH2:17]1)=[O:25])[CH3:30]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 14897375HCID 14897375, compoundHCID 58870794HCID 58870794, compound

Product 2

HCID 222AmmoniaHCID 16666511N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-ethyl-butyramideYield 88.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide (0.030 g, 0.084 mmol), 2-bromo-N,N-diethyl-2-phenyl-acetamide (0.025 g, 0.094 mmol), and Na2CO3 (0.013 g, 0.12 mmol) in DMF (2 mL) was stirred at rt for 18 h. The reaction mixture was diluted with EtOAc (25 mL) and washed with H2O (3×15 mL). The organic layer was dried (Na2SO4) and concentrated. Chromatography of the resulting residue (SiO2; 2 M NH3 in MeOH/DCM) gave the title compound (0.018 g, 38%). MS (ESI): mass calcd. for C28H39FN4O2, 482.31. m/z found, 483.5 [M+H]+. 1H NMR (CDCl3): 7.53-7.45 (m, 3H), 7.38-7.31 (m, 3H), 7.10-7.07 (m, 1H), 6.89-6.84 (m, 1H), 3.50-3.37 (m, 2H), 3.30-3.15 (m, 2H), 3.08 (s, 4H), 2.70 (br s, 4H), 2.05-2.01 (m, 1H), 1.75-1.68 (m, 2H), 1.60-1.52 (m, 2H), 1.09-1.02 (m, 6H), 0.97-0.91 (m, 6H).

Workup

  1. washwashed with H2O (3×15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-60ee2d781f204c6abbda739939fe1448
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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