Isopropylamine → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid isopropylamide

Temperature

90 °C

Trimethylaluminium (0.72 mL of a 2 M solution in toluene, 1.44 mmol) was added dropwise to a stirred solution of isopropylamine (85 mg, 1.44 mmol) in dioxane (3 mL) at room temperature under argon. After 1 h, a solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester (110 mg, 0.36 mmol) in dioxane (3 mL) was added and the reaction mixture heated at 90° C. After 2 h the reaction mixture was cooled in an ice/water bath and quenched with Seignette salt solution (1 mL). The resultant mixture was filtered, the filter cake washed with dichloromethane, then the combined filtrates were concentrated then purified by chromatography (silica, 0 to 80% ethyl acetate in heptane) to give the title compound (45 mg, 38%) as a colourless oil. MS: m/e=333.4 [M+H]+.

1. temperatureAfter 2 h the reaction mixture was cooled in an ice/water bath
2. customquenched with Seignette salt solution (1 mL)
3. filtrationThe resultant mixture was filtered
4. washthe filter cake washed with dichloromethane
5. concentrationthe combined filtrates were concentrated
6. customthen purified by chromatography (silica, 0 to 80% ethyl acetate in heptane)

ORD record

ord-fe949e606ecb4bb8a1293d99331bf34a

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410104B2