Hydroxyamine hydrochloride → 1,1,1-trifluoro-3-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-3-phenylpropan-2-one oxime

HRID 13184

Reaktionsgleichung

[F:1][C:2]([F:31])([F:30])[C:3](O)(O)[CH:4]([O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[N:16]=[CH:15]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[NH2:33][OH:34]>N1C=CC=CC=1>[F:1][C:2]([F:31])([F:30])[C:3](=[N:33][OH:34])[CH:4]([O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[N:16]=[CH:15]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

1,1,1-trifluoro-3-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-3-phenylpropane-2,2-diol (147c) 1.22 g, 2.8 mmol) and hydroxylamine hydrochloride (3.32 g, 48 mmol) was mixed in pyridine (85 mL, dried over 4 Å MS). The mixture was stirred at 115° C. for 30 min, after which time HPLC analysis showed complete reaction. Solvent was evaporated and the residue partitioned between ethyl acetate and water. The phases were separated and the organic phase washed twice with water, followed by brine and then evaporated. The residue was subjected to chromatography (SiO2, gradient of 10-60% Ethyl acetate in Heptane) to afford somewhat impure 1,1,1-trifluoro-3-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-3-phenylpropan-2-one oxime as a 3:7 mixture of diastereomers (0.99 g, 82%).

Aufarbeitung

customreaction
customSolvent was evaporated
customthe residue partitioned between ethyl acetate and water
customThe phases were separated
washthe organic phase washed twice with water
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-b60ba1a4e1934d05b72c250bd520f8a9
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07728030B2

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