Water → 2-cyclopropylamino-1-(3,5-dichloropyridin-2-yl)ethanone-O-methyloxime
Reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1)[CH2:5]Br.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.O>C(#N)C>[CH3:1][O:2][N:3]=[C:4]([C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][N:8]=1)[CH2:5][NH:18][CH:15]1[CH2:17][CH2:16]1Participants
Procedure
To 700 mg of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-methyloxime prepared in the same manner as in Steps 1 to 3 in Synthetic Example 2 in 10 ml of acetonitrile, 402 mg of cyclopropylamine in 5 ml of acetonitrile was added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 30 ml of water and extracted with ethyl acetate (40 ml×2, the resulting organic layers were combined, washed with water (30 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 3:7 to 5:5) as the eluent to obtain 450 mg of the desired product as a colorless resinous substance.
Workup
- customAfter completion of the reaction
- extractionextracted with ethyl acetate (40 ml×2
- washwashed with water (30 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-2cb74b8ae54440ee936cacdd9149db00
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434684B2
Reaction notes
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