Pyridine → HCID 22622556, compound

Participants

Reaction Conditions

Reaction Steps

6-[N-(5-Chloro-2-(2-methylpropoxy )benzyl)-N-ethylamino]pyridazine-3-carboxylic acid (example 10) (2.0 g) was dissolved in pyridine (30 ml) under argon and cooled to 4° C. Methanesulphonyl chloride (0.75 ml, 9.7 mmol) was added to the mixture which was stirred at 4° C. for 1.5 hours to give a dark purple solution. Ammonia gas was then bubbled through the solution for 2 minutes to give a dark red solution (exotherm to +15° C.) and the solution evaporated under reduced pressure. The residue was dissolved in pyridine (30 ml) and cooled under argon to 4° C. Methanesulphonyl chloride (5.1 ml, 66 mmol) was then added dropwise (exotherm to 10° C.) and the resultant brown suspension stirred at ambient temperature overnight. The brown solution was then evaporated and the residue partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organic layer was washed with 10% 2N HCl/saturated aqueous ammonium chloride (×2), saturated aqueous sodium bicarbonate (×1) and brine (×1), dried over Na2SO4, filtered and evaporated. The title product was isolated by column chromatography using 20% ethyl acetate/isohexane as eluant (1.18 g, 62.2%). [OPPI 14: 396-9 (1982)].

Provenance & Evidence