Ammonia → HCID 9847665, compound

Participants

Reaction Steps

To a stirring solution of Compound 56 (80 mg, 0.17 mmol) in DCM (2 mL) and DMF (0.5 mL) was added HOBT (25.7 mg, 0.19 mmol) and DCC (37 mg, 0.18 mmol). The reaction was stirred at room temperature for 30 min, then 28% aqueous NH3 (15 mg, 0.36 mmol) was added. The reaction stirred at room temperature overnight. The reaction mixture was filtered and the filtered solid was washed with DCM (2 mL). The filtrate was diluted with ethyl acetate (6 mL), washed twice with NaHCO3 (2 mL), dried (Na2SO4) and evaporated in vacuo. The crude product was purified via flash column chromatography (DCM:MeOH:NH4OH 93:5:2) to give Compound 58 (36.7 mg, 46%). Compound 58 was dissolved in methanol and treated with 1N HCl/CH3CN (2:1) and lyophilized to give the HCl salt. 1HNMR (DMSO-d6) δ 11.2 (s, 1H), 9.11 (s, 1H), 9.03 (s, 1H), 8.45 (s, 1H), 8.32 (d, J=12.0, 2H), 7.80 (s, 1H), 7.58–7.47 (m, 3H), 7.34–7.01 (m, 3H), 6.42 (s, 1H), 3.34 (s, 3H). ES-MS m/z 473 (MH+).

Provenance & Evidence