Ethylenediamine → HCID 178454516, compound

Participants

Reaction Steps

The solution of compound 10 (170 mg, 0.5 mmol) and ethylenediamine (601 mg, 10 mmol) in methanol (10 mL), water (5 mL) and chloroform (2.5 mL) was refluxed for 24 h. The solvents were evaporated, the residue dissolved in aqueous potassium hydroxide (15 mL, 1 M), and extracted with methylene chloride (4×15 mL). The combined organic phases were washed with water and brine, dried over magnesium sulfate, and the residue chromatographed on silica gel using chloroform—chloroform:methanol (10%) step-gradient as an eluent to give pure MPD021 (113 mg, 62%) as orange crystals. 1H NMR (400 MHz, DMSO-d6): δ 8.15 (d, J=8.4 Hz, 2H), 7.93-7.86 (m, 4H), 7.46 (d, J=8.4 Hz, 2H), 4.35 (s, 2H), 3.98 (t, J=6.0 Hz, 2H), 3.13 (t, J=6.0 Hz, 2H), 2.06 (t, J=7.2 Hz, 2H), 1.54-1.58 (m, 2H), 0.83 (t, J=7.2 Hz, 3H). 13C NMR (100.61 MHz, DMSO-d6): δ 174.22, 166.43, 155.51, 153.37, 139.21, 137.12, 127.14, 127.09, 122.89, 122.78, 61.11, 43.66, 42.69, 37.04, 19.14, 13.06. HRMS (m/z): [M+H]+ calcd. for C20H25N5O2 368.2081. found 368.2099.

Provenance & Evidence