Potassium Hydroxide → HCID 118432073, compound

HRID 2208066Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][CH:22]=[C:23]([C:25]([O:27]C)=[O:26])[CH:24]=3)=[CH:15][CH:14]=2)[CH2:11][C:10]([C:29]([C:35]([F:38])([F:37])[F:36])([C:31]([F:34])([F:33])[F:32])[OH:30])=[N:9]1.[OH-].[K+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:20]=[N:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[CH:24]=3)=[CH:17][CH:18]=2)[CH2:11][C:10]([C:29]([C:31]([F:34])([F:32])[F:33])([C:35]([F:36])([F:38])[F:37])[OH:30])=[N:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 1-(2-chloro-phenyl)-5-(4-(5-methoxycarbonyl-pyridin-3-yl)-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (6.0 mg, 0.01 mmol) prepared in Example 273 in methanol (0.5 mL), was added a solution of potassium hydroxide (2.0 mg, 0.03 mmol) in distilled water (0.5 mL). The reaction mixture was stirred at 70° C. for 2 hours and then washed with diethyl ether. A 1N hydrochloric acid solution was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated solution of sodium hydrogen carbonate and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 5.0 mg of the titled compound as a pale yellow liquid.

Workup

washwashed with diethyl ether
additionA 1N hydrochloric acid solution was added to the reaction mixture, which
extractionwas then extracted with ethyl acetate
washThe extract was washed with a saturated solution of sodium hydrogen carbonate and brine
dry with materialdried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-376610bd327146c6bed9b081a35e0c4f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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