Water → N-[2-(3,5-dichloropyridin-2-yl)-2-(methoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 56031Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:9](=O)[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.[CH3:26][O:27][NH2:28].N1C=CC=CC=1.O>C(O)C>[Cl:1][C:2]1[C:3]([C:9](=[N:28][O:27][CH3:26])[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 200 mg of the N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide prepared in Step 1 in Synthetic Example 15 and 133 mg of methoxyamine hydrochloride in 2.7 ml of ethanol, 168 mg of pyridine was added, and the mixture was stirred at 80° C. for 6 hours. After completion of the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (10 ml×1), the resulting organic layer was washed with water (10 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 191 mg of the desired product as a pale yellow resinous substance.

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate (10 ml×1)
washthe resulting organic layer was washed with water (10 ml×1)
dry with materialdried over saturated aqueous sodium chloride
customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-7fa1ef6b60d7417aa404a1c49edf31ad
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434684B2

Reaction notes

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