Dimethylformamide → 4-{[(4-amino-2-ethylthiazolo[4,5-c]quinolin-7-yl)oxy]methyl}-N-[2-(1H-indol-2-yl)ethyl]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol (245 mg, 1.0 mmol), cesium carbonate (1.3 g, 4.0 mmol), and DMF (20 mL) was stirred at 75° C. for 10 minutes. {[4-(Bromomethyl)phenyl]sulfonyl}[2-(indol-3-yl)ethyl]amine (432 mg, 1.1 mmol) was added in portions over a period of 30 minutes. Several small additions of {[4-(bromomethyl)phenyl]sulfonyl}[2-(indol-3-yl)ethyl]amine were made over several hours. The reaction mixture was diluted with water (250 mL) and then extracted with chloroform (3×100 mL). The extracts were combined and concentrated under reduced pressure. The residue was purified by HPFC eluting with a gradient of 0-20% CMA in chloroform over 700 mL and then with 20% CMA in chloroform over 400 mL. The resulting solid was recrystallized from 100:1 acetonitrile:water to provide 6 mg of 4-{[(4-amino-2-ethylthiazolo[4,5-c]quinolin-7-yl)oxy]methyl}-N-[2-(1H-indol-2-yl)ethyl]benzenesulfonamide as an off-white solid, mp 100.0-101.0° C. MS (APCI) m/z 558 (M+H)+; Anal. calcd for C29H27N5O3S2: C, 62.46; H, 4.88; N, 12.56. Found C, 62.27; H, 4.63; N, 12.73.

Provenance & Evidence