Ozone → HCID 58443395, compound

HRID 2067969Notes

Reaction equation

HRID 2067969 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C@@H:9]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:20]=2[CH3:21])=[O:15])[CH2:10][CH:11]=C)[CH:6]=[CH:7][CH:8]=1.[O:31]=[O+][O-]>C(Cl)Cl>[O:31]=[CH:11][CH2:10][C@H:9]([NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:20]=1[CH3:21])=[O:15])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:30])([F:29])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24823OzoneHCID 58443391HCID 58443391, compound

Product 1

HCID 58443395HCID 58443395, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [(S)-1-(3-trifluoromethyl-phenyl)-but-3-enyl]-amide (400 mg, 0.92 mmol) in CH2Cl2 (25 mL) at −78° C. is treated with ozone gas by bubbling for 30 min until a blue color is sustained. After stiffing for an additional hour at −78° C., dimethylsulfide (4.2 mL) is added. The reaction mixture is warmed to room temperature and concentrated in vacuo to afford 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [(S)-3-oxo-1-(3-trifluoromethyl-phenyl)-propyl]-amide (390 mg, 98%) which is used without further purification.

Workup

  1. customby bubbling for 30 min until a blue color
  2. waitAfter stiffing for an additional hour at −78° C.
  3. additiondimethylsulfide (4.2 mL) is added
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc351f1fe3154e6d9a4a5816333d1b34
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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