Ozone → HCID 58443382, compound

HRID 2067972Notes

Reaction equation

[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C@@H:9]([NH:15][C:16]([C:18]2[CH:19]=[N:20][N:21]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:22]=2[CH3:23])=[O:17])[CH2:10][CH2:11][CH2:12][CH:13]=C)[CH:6]=[CH:7][CH:8]=1.[O:33]=[O+][O-]>C(Cl)Cl>[O:33]=[CH:13][CH2:12][CH2:11][CH2:10][C@H:9]([NH:15][C:16]([C:18]1[CH:19]=[N:20][N:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:22]=1[CH3:23])=[O:17])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:32])([F:31])[F:1])[CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [(S)-1-(3-trifluoromethyl-phenyl)-hex-5-enyl]-amide (800 mg, 1.7 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 stirring for an additional hour at −78° C., dimethylsulfide (10 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)-5-oxo-1-(3-trifluoromethyl-phenyl)-pentyl]-amide which is used without further purification.

Workup

customby bubbling for 30 min until a blue color
additiondimethylsulfide (10 mL) is added
temperatureThe reaction mixture is warmed to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-450b1b6fddfd4b15b7657d59300fe100
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293917B2

Reaction notes

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