Methylamine → HCID 178485040, compound

Participants

Reaction Steps

1-(2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one (66 mg, 0.158 mmol) was weighed into a flask, then dissolved in 2.0 mL IPA. Triethylamine (0.055 ml, 0.38 mmol) was then added followed by diphenyl cyanocarbonimidate (75 mg, 0.316 mmol). The reaction was then stirred at room temperature for 1.5 hours. The reaction was then transferred to a scaled tube, followed by addition of 3 mL of methyl amine (2.4 ml, 4.9 mmol) in MeOH. The reaction was then placed in a 60° C. bath for 12 hours. The reaction vas then removed and concentrated, and the residue was purified by flash column chromatography (3-7% MeOH/CH2Cl2) to provide the desired product (32 mg, 41%) as a light orange foam film. MS ESI (+) m/z 499 (M+E) detected; 1H NMR (400 MHz, MeOH) δ 7.48 (m, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.38 (m, 2H), 7.28 (m, 3H), 3.45 (m, 1H), 3.39 (m, 1H), 3.27 (m, 1H), 2.78 (s, 3H), 2.45 (m, 1H), 1.99 (m, 1H), 1.59 (m, 1H), 1.39 (s, 9H).

Provenance & Evidence