Triethylamine → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-amide

HRID 42727Notes

Reaction equation

[CH3:1][O:2][NH:3][CH:4]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:12])=[CH:8][C:7]1([CH3:14])[CH3:13])[CH3:5].C(N(CC)CC)C.[F:22][CH:23]([F:33])[C:24]1[C:28]([C:29](Cl)=[O:30])=[CH:27][N:26]([CH3:32])[N:25]=1>ClCCl>[CH3:1][O:2][N:3]([CH:4]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:12])=[CH:8][C:7]1([CH3:13])[CH3:14])[CH3:5])[C:29]([C:28]1[C:24]([CH:23]([F:33])[F:22])=[N:25][N:26]([CH3:32])[CH:27]=1)=[O:30]

Participants

Conditions

Temperature: 24 °C

Procedure

To a stirred solution of O-methyl-N-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-hydroxylamine (diastereomere B), prepared as described in example P7, (58 mg; 0.29 mmol) and triethylamine (50 μl; 0.35 mmol) in dichloromethane (1.2 ml) was added dropwise 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (57 mg; 0.29 mmol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen. The mixture was concentrated to an oil which was subject to flash-master column chromatography (Elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99) to afford 80 mg (78% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-amide as a clear oil.

Workup

concentrationThe mixture was concentrated to an oil which
washwas subject to flash-master column chromatography (Elution gradient: cyclohexane/ethyl acetate 99:1 to 1:99)

Sources & evidence

ORD record: ord-fb55f8f31a5e4245b4e7030285458432
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536215B2

Reaction notes

Loading…