Potassium Carbonate → HCID 16667280, compound

HRID 1927605Notes

Reaction equation

HRID 1927605 reaction equation
Cl.Cl.[CH2:3]([CH:5]([CH2:22][CH3:23])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[C:11]([F:21])[CH:10]=1)=[O:7])[CH3:4].[CH3:24][O:25][C:26](=[O:37])[CH:27](Br)[C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:24][O:25][C:26](=[O:37])[CH:27]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[N:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[CH:5]([CH2:3][CH3:4])[CH2:22][CH3:23])=[CH:10][C:11]=2[F:21])[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4625673Methyl 2-bromo-2-(4'-cyanophenyl)acetateHCID 693036372-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide dihydrochloride

Product 1

HCID 16667280HCID 16667280, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide dihydrochloride (0.06 g, 0.16 mmol), bromo-(4-cyano-phenyl)-acetic acid methyl ester (0.05 g, 0.20 mmol), and anhydrous K2CO3 (0.08 g, 0.55 mmol) in DMF (5 mL) was stirred at rt for 20 h. The mixture was diluted with water (100 mL) and extracted with DCM (2×30 mL). The combined organic phases were washed with water, dried (Na2SO4), and concentrated. The residue was purified (SiO2; acetone/DCM) to give the title compound (0.06 g, 79%). MS: mass calcd. for C26H31FN4O3, 466.24. m/z found, 467.4 [M+H]+. 1H NMR (CDCl3): 7.68-7.60 (m, 4H), 7.45 (dd, J=14.0, 2.4, 1H), 7.27 (br s, 1H), 7.13-7.08 (m, 1H), 6.85 (t, J=9.0, 1H), 4.14 (s, 1H), 3.72 (s, 3H), 3.10-3.03 (m, 4H), 2.69-2.56 (m, 4H), 2.04-1.95 (m, 1H), 1.74-1.62 (m, 2H), 1.59-1.48 (m, 2H), 0.92 (t, J=7.4, 6H).

Workup

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified (SiO2; acetone/DCM)

Sources & evidence

ORD record
ord-b0613245750d4f0c882c1d91c9252f1a
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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