m-Chloroperbenzoic acid → 4-[4-(4-Fluorophenyl)-2-methyl-5-(2-methanesulfonyl-pyrimidin-4-yl)-3-oxo-2,3-dihydro-pyrazol-1-yl]-piperidine-1 carboxylic acid tert-butyl ester

HRID 1838867Notes

Reaction equation

HRID 1838867 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21](SC)[N:20]=3)=[C:17]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:16](=[O:34])[N:15]2[CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:37]1C=CC=C(C(OO)=O)C=1.[S:47](=[O:50])(O)[O-:48].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([S:47]([CH3:37])(=[O:50])=[O:48])[N:20]=3)=[C:17]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[C:16](=[O:34])[N:15]2[CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 116989724-[4-(4-Fluorophenyl)-2-methyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-2,3-dihydro-pyrazol-1-yl]-piperidine-1 carboxylic acid tert-butyl esterHCID 23665763Sodium Bisulfite

Product 1

HCID 600611314-[4-(4-Fluorophenyl)-2-methyl-5-(2-methanesulfonyl-pyrimidin-4-yl)-3-oxo-2,3-dihydro-pyrazol-1-yl]-piperidine-1 carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-[4-(4-fluorophenyl)-2-methyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-3-oxo-2,3-dihydro-pyrazol-1-yl]-piperidine-1 carboxylic acid tert-butyl ester, 11, (5.9 g, 12 mmol) in CHCl3 (200 mL) at 0° C. is added meta-chloroperbenzoic acid (4 g, 23.37 mmol). After stirring for 5 minutes, saturated sodium bisulfite (20 mL) is added and the reaction mixture stirred for an additional 5 minutes. The aqueous phase is extracted three times with CH2Cl2, the combined organic phases washed with saturated sodium bicarbonate, dried (MgSO4), filtered and concentrated in vacuo. The crude material is used without further purification.

Workup

  1. stirringthe reaction mixture stirred for an additional 5 minutes
  2. extractionThe aqueous phase is extracted three times with CH2Cl2
  3. washthe combined organic phases washed with saturated sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material is used without further purification

Sources & evidence

ORD record
ord-73366fa6ac374c59ad8452392cd8e0be
Source dataset
uspto-grants-2004_01
Patent number
US06677337B2

Reaction notes

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