4-Aminomethyltetrahydropyran → HCID 44193423, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-N-(3-tert-butyl-isoxazol-5-yl)-2-methyl-propionamide (0.25 g, 0.87 mmol, prepared according to method C, step 1)) and 1-tetrahydro-2H-pyran-4-ylmethane-amine (0.20 g, 1.73 mmol) in acetonitrile/water (95/5, 4 mL) is added silver (I) oxide (0.80 g, 3.68 mmol). The reaction is heated to 60° C. for 18 h. After cooling, the reaction mixture is filtered through a plug of Na2SO4/cotton wool. The filtrate is concentrated under reduced pressure to give a brown oil, which is purified by mass-triggered preparative LC (neutral conditions) to afford N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-[(tetrahydro-pyran-4-ylmethyl)-amino]-propionamide (28 mg, 10%). m/z 324 [M+H+]. The hydrochloride salt of the title compound is formed by trituration with 1M HCl solution in ether.

Provenance & Evidence