Dicyclohexylcarbodiimide → 3-({4-[3-(3,4-Dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}carbonyl)phenyl acetate

HRID 524145

Reaction equation

HRID 524145 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[C:26]([O:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](O)=[O:34])(=[O:28])[CH3:27].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:26]([O:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:32]([C:33]([N:20]2[CH2:21][CH2:22][CH:17]([N:15]3[C:14](=[O:23])[C:13]([CH3:25])([CH3:24])[C:12]([C:6]4[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=4)=[N:16]3)[CH2:18][CH2:19]2)=[O:34])[CH:31]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2386693-Acetoxybenzoic acidHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 462027213-({4-[3-(3,4-Dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}carbonyl)phenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 g 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one (compound B1), 8 g of 3-(acetyloxy)benzoic acid and 7 g of DCC in 150 ml of DCM is stirred for 2 h until the reaction is complete according to TLC analysis. The reaction mixture is quenched with water, the phases are separated and the organic phase is washed with water again. The organic phase is dried over MgSO4, and the solvent is removed under reduced pressure resulting in a crude product, which is purified by crystallization from methanol to yield the title compound.

Workup

  1. customThe reaction mixture is quenched with water
  2. customthe phases are separated
  3. washthe organic phase is washed with water again
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvent is removed under reduced pressure
  6. customresulting in a crude product, which
  7. customis purified by crystallization from methanol

Sources & evidence

ORD record
ord-00e8849f8046435882f0a5e8979fbacf
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Linked notes

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