Acetyl chloride → HCID 46202402, compound

HRID 1914149Notes

Reaction equation

HRID 1914149 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:34])=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[C:18]([C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=4)=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[CH:7]=1.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[Cl:34][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:35](=[O:37])[CH3:36])=[CH:7][C:6]=1[C:8]([N:10]1[CH2:11][CH2:12][CH:13]([N:16]2[C:20](=[O:21])[C:19]([CH3:23])([CH3:22])[C:18]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)=[N:17]2)[CH2:14][CH2:15]1)=[O:9]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 46202401HCID 46202401, compound

Product 1

HCID 46202402HCID 46202402, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.18 g of 2-{1-[(5-amino-2-chlorophenyl)carbonyl]piperidin-4-yl}-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound described in example 91) are dissolved in 5 ml of DCM, 0.17 ml TEA and 0.032 ml acetyl chloride are added, and the reaction mixture is stirred at RT for about 16 h until the reaction is completed according to TLC analysis. The mixture is washed with 0.5 M aqueous sulfuric acid, twice with 1 M aqueous sodium carbonate solution and with brine. The organic phase is dried over MgSO4, and the solvent is removed under reduced pressure resulting in the crude product, which is purified by column chromatography (silica gel and EA) yielding the title compound.

Workup

  1. washThe mixture is washed with 0.5 M aqueous sulfuric acid, twice with 1 M aqueous sodium carbonate solution and with brine
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is removed under reduced pressure
  4. customresulting in the crude product, which
  5. customis purified by column chromatography (silica gel and EA)

Sources & evidence

ORD record
ord-f6e3555f657f4ad9b34c1240f4ba86be
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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