4-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

HRID 594139

Reaktionsgleichung

[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:19])[O:4][N:3]=1.[CH:20]([C:23]1[CH:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=1)([CH3:22])[CH3:21]>N1C=CC=CC=1>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([CH:20]([CH3:22])[CH3:21])=[CH:28][N:27]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:19])[O:4][N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a stirred solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride (500 mg, 1.66 mmol) in pyridine (5 mL) at 25° C. was added 5-isopropylpyridin-2-amine (226 mg, 1.66 mmol). The reaction mixture was stirred at 25° C. for 2 hours, then left to stand at this temperature overnight. The crude reaction mixture was then purified by flash silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and concentrated in vacuo to give the title compound (454 mg) as an orange solid. LCMS (2 min, formic) Rt 1.00 min, m/z (ES+) 402 (M+H).

Aufarbeitung

waitleft
customto stand at this temperature overnight
customThe crude reaction mixture
customwas then purified by flash silica (Si) chromatography (0-50% ethyl acetate-cyclohexane gradient)
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-86292c7b231141f9b8b0e41431a13e18
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09242972B2

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