2-Ethylbutyryl chloride → HCID 16667232, compound

HRID 1927602Notes

Reaction equation

HRID 1927602 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15](=[O:21])[CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH2:10][CH2:9]2)=[C:4]([F:28])[CH:3]=1.[CH2:29]([CH:31]([CH2:35][CH3:36])[C:32](Cl)=[O:33])[CH3:30]>C(Cl)Cl>[CH2:17]([CH:16]([CH2:19][CH3:20])[C:15]([N:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:32](=[O:33])[CH:31]([CH2:35][CH3:36])[CH2:29][CH3:30])=[CH:3][C:4]=2[F:28])[CH2:9][CH2:10]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21])[CH3:18]

Participants

4

Reactant 2

HCID 759542-Ethylbutyryl chlorideHCID 69305096N-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-2-ethyl-N-phenyl-butyramide

Product 1

HCID 16667232HCID 16667232, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-[1-(4-amino-2-fluoro-phenyl)-piperidin-4-yl]-2-ethyl-N-phenyl-butyramide (0.30 mmol) and TEA (2.0 mmol) in DCM (10 mL) was added 2-ethyl-butyryl chloride (1.0 mmol). After 16 h, the mixture was washed with H2O (10 mL). The organic layer was concentrated and the residue was purified by PTLC to provide the title compound (45 mg, 31%). MS (ESI): mass calcd. for C29H40FN3O2, 481.31. m/z found, 482.4 [M+H]+. 1H NMR (CDCl3): 7.50-7.35 (m, 5H), 7.15-7.03 (m, 2H), 6.86 (t, J=8.8, 1H), 4.90-4.72 (m, 1H), 3.44-3.30 (m, 2H), 2.80-2.67 (m, 2H), 2.30-1.30 (m, 14H), 0.95 (t, J=7.3, 6H), 0.80 (t, J=7.2, 6H).

Workup

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

Sources & evidence

ORD record
ord-9e3d8683b99f4ee499cb92dd3c979491
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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