Water → 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-(3,5-dimethyl-2-pyridinyl)benzenesulfonamide

HRID 594127

Reaktionsgleichung

Reaktionsgleichung von HRID 594127
N1C=CC=CC=1.[CH3:7][C:8]1[C:9]([NH2:15])=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=1.[CH3:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[C:20]([CH3:34])[O:19][N:18]=1.O>ClCCl>[CH3:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:25]=[CH:26][C:27]([S:30]([NH:15][C:9]3[C:8]([CH3:7])=[CH:13][C:12]([CH3:14])=[CH:11][N:10]=3)(=[O:32])=[O:31])=[CH:28][CH:29]=2)=[C:20]([CH3:34])[O:19][N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 30163103,5-Dimethylpyridin-2-amineHCID 164907024-((3,5-Dimethylisoxazol-4-yl)methoxy)benzene-1-sulfonyl chloride

Produkt 1

HCID 898763854-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-(3,5-dimethyl-2-pyridinyl)benzenesulfonamideAusbeute 14,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of pyridine (0.083 mL, 1.023 mmol) and 3,5-dimethyl-2-pyridinamine (125 mg, 1.023 mmol) in dichloromethane (1 mL) was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (309 mg, 1.023 mmol). The mixture was heated at 70° C. for 4 hours. Water (5 mL) was added and the organic phase separated and purified by flash silica (Si) chromatography (50% dichloromethane-ethyl acetate gradient) to give the title compound (56 mg) as a bright yellow solid. LCMS (2 min, formic) Rt 0.93 min, m/z (ES+) 388 (M+H).

Aufarbeitung

  1. customthe organic phase separated
  2. custompurified by flash silica (Si) chromatography (50% dichloromethane-ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7fb3f83adcf646e390f408c841ceaaa0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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