6-Methoxypyridazin-3-amine → HCID 117925948, Verbindung

HRID 594130

Reaktionsgleichung

[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[C:14]([CH3:28])[O:13][N:12]=1>N1C=CC=CC=1>[CH3:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH:9][C:6]3[N:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[C:14]([CH3:28])[O:13][N:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

To a solution of 6-methoxypyridazin-3-amine (125 mg, 1.0 mmol) in pyridine (8 mL) at room temperature, was added 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (0.302 g, 1.0 mmol). The reaction mixture was stirred at 20° C. for 18 hours. The solvent was evaporated in vacuo and passed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol, followed by a sulphonic acid (SCX) SPE cartridge eluting with methanol. The crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-25% methanol gradient), to provide the title compound (16 mg). LCMS (2 min, formic) Rt 0.83 min, m/z (ES+) 391 (M+H).

Aufarbeitung

customThe solvent was evaporated in vacuo
extractionpassed through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
washeluting with methanol
washeluting with methanol
customThe crude was then purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane+0-25% methanol gradient)

Quellen und Nachweise

ORD-Eintrag: ord-a6f100bcc13f4355b07a0d68d4972464
Quelldatensatz: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09242972B2

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