Triethylamine → HCID 54756257, compound

Participants

Reaction Steps

A solution of dichloromethane (10 mL), compound 41 (100 mg, 0.337 mmol) and triethylamine (141 μL, 1.02 mmol) was cooled to 0° C. 2-chloro-1-ethane sulfonyl chloride (32 μL, 0.304 mmol) was added and the reaction was allowed to proceed for 1 hour prior to removal of a precipitate and addition of saturated sodium bicarbonate (10 mL) and extraction with dichloromethane (2×10 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The product was purified by preparative RP-HPLC and lyophilized (24 mg, 20% yield): 1H NMR (400 MHz, DMSO) δ 10.81 (br, 1H), 10.13 (s, 1H), 8.75 (s, 1H), 8.02 (s, 1H), 7.58 (d, J=8.9, 2H), 7.25 (m, 3H), 6.83 (dd, J=16.4, 10.0, 1H), 6.15 (d, J=16.5, 1H), 6.07 (d, J=10.0, 1H), 3.99 (s, 3H), 3.98 (s, 3H); 13C NMR (100 MHz, DMSO) δ 157.93, 156.16, 150.10, 149.26, 136.23, 135.75, 132.76, 127.82, 125.54, 120.00, 107.16, 103.16, 100.51, 56.55, 56.45; [M+H]+ calculated for C18H18N4O4S 387.1, found 387.4.

Provenance & Evidence