Water → HCID 16665203, compound

HRID 1927616Notes

Reaction equation

HRID 1927616 reaction equation
[CH2:1]([CH:3]([NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:10]([F:20])[CH:9]=1)[CH2:4][CH3:5])[CH3:2].Br[CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24]([NH:26][CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:27]([NH:26][C:24]([CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[N:17]1[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:21])=[CH:9][C:10]=2[F:20])[CH2:15][CH2:16]1)=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12263351HCID 12263351, compoundHCID 69305101HCID 69305101, compound

Product 1

HCID 16665203HCID 16665203, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(1-ethyl-propyl)-3-fluoro-4-piperazin-1-yl-benzamide (12 mg, 0.04 mmol), 2-bromo-N-ethyl-2-phenyl-acetamide (12 mg, 0.05 mmol), and K2CO3 (8 mg, 0.05 mmol) in DMF (2 mL) was stirred for 16 h. The mixture was poured into water and extracted with DCM. The organic layer was dried (MgSO4) and purified by PTLC to give a white solid (6 mg, 34%). MS (ESI): mass calcd. for C26H35FN4O2, 454.58. m/z found, 455.5 [M+H]+. 1H NMR (CDCl3): 7.47-7.42 (m, 2H), 7.34-7.30 (m, 5H), 7.05-7.02 (m, 1H), 6.90 (t, J=8.4, 1H), 5.67 (d, J=8.9, 1H), 3.99-3.94 (m, 1H), 3.89 (s, 1H), 3.37-3.31 (m, 2H), 3.19-3.17 (m, 4H), 2.64-2.55 (m, 4H), 1.66-1.59 (m, 5H), 1.49-1.42 (m, 2H), 1.16 (t, J=7.2, 3H), 0.93 (t, J=7.4, 6H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried (MgSO4)
  3. custompurified by PTLC

Sources & evidence

ORD record
ord-bd5e0e20d8dd4168b82007fa7e2a12d8
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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