Acetyl chloride → HCID 46202402, compound

HRID 524221Notes

Reaction equation

HRID 524221 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-a753630d363e449cb83c2deb16fe3c06
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

Loading…