Methanesulfonyl chloride → HCID 11626998, compound

Participants

Reaction Steps

A solution of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)aniline (50 mg, 0.126 mmol) in dichloromethane (1.5 mL) was added to methanesulfonyl chloride (58 mg, 0.51 mmol) while stirring, followed by the addition of a solution of diisopropylethylamine (18 mg, 0.14 mmol) in dichloromethane (0.5 mL). Stirring was continued for 12 hours at room temperature and then the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate (30 mL), washed with sodium bicarbonate (2×25 mL) and the organic layer was isolated and concentrated. The product was purified by silica gel chromatography using 40% ethyl acetate in hexanes to give 23 mg (40%) of N-[3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)phenyl]methanesulfonamide as a yellow solid. MS [M+H] 474.7. 1H NMR (400 MHz, CDCl3) δ (ppm) 8.65 (s, 1H), 7.42 (m, 2H), 7.23 (t, J=68.0 Hz, 1H), 7.22 (s, 1H), 7.06-7.01 (m, 2H), 6.76 (dd, J=8.0, 2.0 Hz, 1H), 6.68 (t, J=2.4 Hz, 1H), 6.58 (dd, J=8.0, 2.4 Hz, 1H), 6.32 (b, 1H), 4.58 (t, J=6.0 Hz, 2H), 3.01 (s, 3H), 2.07 (m, 2H).

Provenance & Evidence