反应详情

To a solution of 1-(3-aminoquinolin-4-ylamino)-2-methylpropan-2-ol (CAN 129655-59-0, 0.94 g, 4.06 mmol) in dichloromethane (9.5 mL) in an inert atmosphere was added dropwise with stirring at room temperature over a period of 6 min a solution of hexanoyl chloride (422 μl, 4.47 mmol) in dichloromethane (6.4 mL). After 3 h additional hexanoyl chloride (192 μl, 2.03 mmol) was added and stirring continued for another hour and finally the mixture was concentrated in vacuo. The residue was re-dissolved in ethanol (13.5 mL) and, after addition of sodiumhydroxide solution (1 M, 10.8 mL) the mixture was heated with stirring in argon to 90° C. After 75 min the mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was stirred with ethyl acetate (30 mL) and water (5 mL) dried by filtration over ChemElut® and ethyl acetate was removed in vacuo. The residue was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane) to give the title compound (747 mg, 89%) as yellow oil; LC-MS (UV peak area, ESI) 95%, 312.2 (MH+).

1. waitcontinued for another hour
2. concentrationfinally the mixture was concentrated in vacuo
3. dissolutionThe residue was re-dissolved in ethanol (13.5 mL)
4. additionafter addition of sodiumhydroxide solution (1 M, 10.8 mL) the mixture
5. temperaturewas heated
6. stirringwith stirring in argon to 90° C
7. concentrationconcentrated in vacuo
8. stirringThe residue was stirred with ethyl acetate (30 mL) and water (5 mL)
9. dry with materialdried by filtration over ChemElut® and ethyl acetate
10. customwas removed in vacuo
11. customThe residue was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane)