Triethylamine → 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-amide
Reaktionsgleichung
[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]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 24 °C
Versuchsvorschrift
To a stirred solution of O-methyl-N-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-hydroxylamine (diastereomer A), prepared as described in example P7, (88 mg; 0.45 mmol) and triethylamine (75 μl; 0.54 mmol) in dichloromethane (2 ml) was added dropwise 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (87 mg; 0.45 mmol). The reaction mixture was stirred at 24° C. for 16 h under nitrogen atmosphere. 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 106 mg (66% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-amide as an amorph solid.
Aufarbeitung
- 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)
Quellen und Nachweise
- ORD-Eintrag
- ord-acf255cbb19346718d620a1bbad3137a
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08536215B2
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