2-Ethylbutyryl chloride → N-(4-{4-[Diethylcarbamoyl-(3-fluoro-phenyl)-methylene]-piperidin-1-yl}-3-fluoro-phenyl)-2-ethyl-butyramide

HRID 1927621Notes

Reaction equation

HRID 1927621 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[C:4]([F:29])[CH:3]=1.[CH2:30]([CH:32]([CH2:36][CH3:37])[C:33](Cl)=[O:34])[CH3:31]>ClCCCl>[CH2:18]([N:17]([CH2:20][CH3:21])[C:15]([C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)=[C:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:33](=[O:34])[CH:32]([CH2:36][CH3:37])[CH2:30][CH3:31])=[CH:3][C:4]=2[F:29])[CH2:9][CH2:10]1)=[O:16])[CH3:19]

Participants

4

Reactant 2

HCID 759542-Ethylbutyryl chlorideHCID 69304055HCID 69304055, compound

Product 1

HCID 58870632N-(4-{4-[Diethylcarbamoyl-(3-fluoro-phenyl)-methylene]-piperidin-1-yl}-3-fluoro-phenyl)-2-ethyl-butyramideYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 2-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-ylidene]-N,N-diethyl-2-(3-fluoro-phenyl)-acetamide (0.33 mmol) and TEA (2.0 mmol) in DCE (10 mL) was added 2-ethylbutyryl chloride (1 mmol) dropwise. The mixture was stirred at rt for 16 h, then was washed with H2O (10 mL). The organic layer was concentrated and the residue was purified by PTLC to provide the title compound (54 mg, 33%). MS (ESI): mass calcd. for C29H37F2N3O2, 497.29. m/z found, 498.4 [M+H]+. 1H NMR (CDCl3): 7.58-7.53 (m, 1H), 7.47 (NH, 1H), 7.37-7.32 (m, 1H), 7.18-7.06 (m, 3H), 7.04-6.97 (m, 1H), 6.92-6.85 (m, 1H), 3.50-3.00 (m, 6H), 2.62-2.52 (m, 4H), 2.10-2.02 (m, 1H), 1.79-1.67 (m, 4H), 1.62-1.52 (m, 2H), 1.16 (t, J=7.1, 3H), 1.00-0.87 (m, 9H).

Workup

  1. washwas washed with H2O (10 mL)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by PTLC

Sources & evidence

ORD record
ord-2e53d811bcb74012ba4db6e511dd77dd
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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