Chloroacetyl chloride → HCID 54756017, compound

Participants

Reaction Steps

A solution of THF (20 mL), compound 22 (200 mg, 0.75 mmol) and DIPEA (143 μL, 0.821 mmol) was cooled to 0° C. Chloroacetylchloride (54 μL, 0.67 mmol) was added and the reaction was allowed to proceed for 1 hour and afterwards concentrated in vacuo. The residue was dissolved in dichloromethane (20 mL) and washed with saturated sodium bicarbonate (20 mL). The aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The product was purified by preparative RP-HPLC and lyophilized (30.4 mg, 13% yield): 1H NMR (400 MHz, DMSO) δ 10.57 (s, 1H), 8.41 (s, 1H), 7.95 (s, 1H), 7.67 (d, J=7.6, 1H), 7.53 (t, J=7.9, 1H), 7.41 (d, J=7.7, 1H), 5.11 (hept, J=6.7, 1H), 4.30 (s, 2H), 1.51 (d, J=6.7, 6H); 13C NMR (100 MHz, DMSO) δ 165.06, 154.82, 151.89, 150.90, 144.68, 139.03, 132.62, 128.28, 123.81, 120.02, 119.24, 96.92, 48.84, 43.55, 21.77; [M+H]+ calculated for C16H17ClN6O 345.1, found 345.4.

Provenance & Evidence