Piperazine → HCID 3863656, compound

Participants

Reaction Steps

Method B (14, 20, 23, 32). 2-[4-(5-Chloro-thiophene-2-sulfonyl)-piperazin-1-yl]-6,7-dimethoxy-quinazolin-4-ylamine (14): To a solution of piperazine (0.517 g, 6.0 mmol) and 5-chloro-thiophene-2-sulfonyl chloride (0.436 g, 2.0 mmol) in methanol (10 mL), the mixture was stirred at room temperature for 1 h. The solvent was evaporated, and the residue was purified with silica gel chromatography to obtain 1-(5-chloro-thiophene-2-sulfonyl)-piperazine. The intermediate (0.266 g, 1.0 mmol) and 4-amino-2-chloro-6,7-dimethoxy-quinazoline (0.251 g, 1.0 mmol) in 1-butanol (5 mL) were stirred under reflux overnight, and cooled to 80° C. The collected solid product was washed with ethyl acetate (2×10 mL), stirred in methanol (30 mL) under reflux for 1 h, filtered, washed with methanol (2×10 ml) to yield compound 14. 1HNMR (DMSO-d6) δ 3.06-3.08 (m, 4H), 3.80 (s, 3H), 3.84 (s, 3H), 3.94 (s, 4H), 7.36 (s, 1H), 7.37 (s, 1H), 7.59 (s, 1H), 7.60 (s, 1H). HRMS (M+H)+ calcd for C18H21ClN5O4S2 470.0718, found 470.0740. Anal. (C18H20ClN5O4S2.HCl) C, H, N.

Provenance & Evidence