Diisopropylethylamine → 6-[N-(5-Chloro-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-sulphonamide

HRID 1870750

Reaktionsgleichung

[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[CH3:2].Cl[C:18]1[N:19]=[N:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:5]([CH:10]=1)[CH2:4][N:3]([C:18]1[N:19]=[N:20][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1)[CH2:1][CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A mixture of N-ethyl-5-chloro-2-(2-methylprop-2-en-1-yloxy)benzylamine (2.76 g, 10 mmol), 3-chloro-pyridazine-6-sulphonamide [Archiv der Pharmazie (1966) 299, 646-650 and EP patent no 96,004] (1.5 g, 7.8 mmol) and ethyl di-isopropylamine (10 ml, 57 mM) in DMF (50 ml) was stirred at 130° C. for 16 hours under a reflux condenser. The solvent was evaporated at reduced pressure and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was separated, dried over anhydrous magnesium sulphate, filtered and evaporated to give a brown gum (2.5 g). The brown gum was purified by chromatography on silica, eluting with a gradient of 0→20% ethyl acetate in dichloromethane to give the title compound as a yellow solid (600 mg).

Aufarbeitung

customThe solvent was evaporated at reduced pressure
customthe residue partitioned between dichloromethane (100 ml) and water (100 ml)
customThe organic layer was separated
dry with materialdried over anhydrous magnesium sulphate
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-2b55a7a92bba4d43b90f9c0df0d36d3a
Quelldatensatz: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06100258

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