Triethylamine → HCID 54672820, compound

HRID 1039345Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([NH:13][O:14][CH3:15])[CH2:11][F:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:23][CH:24]([F:34])[C:25]1[C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]([CH3:33])[N:26]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH:10]([N:13]([O:14][CH3:15])[C:30]([C:29]2[C:25]([CH:24]([F:34])[F:23])=[N:26][N:27]([CH3:33])[CH:28]=2)=[O:31])[CH2:11][F:12])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 24 °C

Procedure

To a stirred solution of N-[3-(4-chlorophenyl)-1-fluoromethyl-propyl]-O-methyl-hydroxylamine (60 mg; 0.26 mmol), prepared as described in example P8c and triethylamine (0.05 ml; 0.31 mmol) in dichloromethane (1 ml) under nitrogen was added drop wise 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (51 mg; 0.26 mmol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen. The mixture was washed with 1M sodium hydroxide (20 ml), 1M hydrochloric acid (20 ml) and brine (20 ml). Organics were dried over sodium sulfate and evaporated under reduced pressure. The crude was subject to flash chromatography (eluant: c-hexane/ethyl acetate 90:10 to 70:30) to afford 67 mg (66% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [3-(4-chloro-phenyl)-1-fluoromethyl-propyl]-methoxy-amide as a clear oil.

Workup

washThe mixture was washed with 1M sodium hydroxide (20 ml), 1M hydrochloric acid (20 ml) and brine (20 ml)
dry with materialOrganics were dried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-85a549749b7f407eb2099754bba4f4f0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552049B2

Reaction notes

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