Water → 1-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-[1-(5-ethyl-pyrimidin-2-yl)-piperidin-4-yl]-oxime

HRID 2066903Notes

Reaction equation

HRID 2066903 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[C:19]([F:21])[C:18]([Br:22])=[CH:17][C:16]=3[F:23])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.Cl[C:25]1[N:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][N:26]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O.CCOC(C)=O>[CH2:31]([C:28]1[CH:27]=[N:26][C:25]([N:1]2[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]3[CH2:14][CH2:13][N:12]([C:15]4[CH:20]=[C:19]([F:21])[C:18]([Br:22])=[CH:17][C:16]=4[F:23])[CH2:11][CH2:10]3)[CH2:3][CH2:2]2)=[N:30][CH:29]=1)[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 866550281-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Product 1

HCID 866550291-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-[1-(5-ethyl-pyrimidin-2-yl)-piperidin-4-yl]-oxime

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 77b and 2-chloro-5-ethyl-pyrimidine (300 mg) were heated with diisopropylethylamine (300 mg) in DMSO at 130° C. for 0.5 h. Water and EtOAc were added and the organic phase separated, dried over MgSO4 and concentrated. The mixture was purified by chromatography on silica gel eluting with EtOAc/Hexane to give 1-(4-bromo-2,5-difluoro-phenyl)-piperidin-4-one O-[1-(5-ethyl-pyrimidin-2-yl)-piperidin-4-yl]-oxime 77c (170 mg).

Workup

  1. customthe organic phase separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe mixture was purified by chromatography on silica gel eluting with EtOAc/Hexane

Sources & evidence

ORD record
ord-a5d3ba83d9f64223a822d77c5a7dccc7
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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