HCID 59551899, compound → HCID 11646432, compound

Participants

Reaction Steps

A solution of benzo[1,3]dioxol-5-ylmethyl-{3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester (10.6 g, 22.4 mmol) in TFA/DCM (50%, 70 mL) was stirred at room temperature for 30 min. The solvent was evaporated and a saturated solution of potassium carbonate (50 mL) was added to make it basic (pH 9). The solution was extracted with ethyl acetate (2×200 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent gave 8.30 g (99%) of N′-benzo[1,3]dioxol-5-ylmethyl-N-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N-methyl-propane-1,3-diamine as a colorless oil. [M+H]+ 373.26; 1H-NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 7.63 (s, 1H), 7.07 (s, 1H), 6.79 (s, 1H), 6.72 (s, 2H), 5.92 (s, 2H), 3.67 (s, 3H), 3.60 (br s, 1H), 3.10 (br s, 2H), 2.66 (t, 2H), 2.0 (br s, 2H), 1.87 (q, 2H); 13C-NMR (100 MHz, CD3OD) δ 184.3, 156.7, 147.7, 146.6, 136.4, 133.8, 129.9, 121.2, 117.1, 108.6, 108.1, 100.9, 53.7, 45.7, 27.1.

Provenance & Evidence