Methylamine → HCID 178485043, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide (61 mg, 0.145 mmol, prepared as described in WO 2006/044825 Example 121) was weighed into a flask, then dissolved in 2.0 mL IPA. Triethylamine (0.051 ml, 0.362 mmol) was then added, followed by diphenyl cyanocarbonimidate (69 mg, 0.290 mmol). The reaction was stirred at 23° C. for 1.5 hours, then transferred to a pressure 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 and then concentrated. The residue was purified by flash column chromatography (3-7% MeOH/DCM) affording the desired product (27 mg, 37%) as an orange foam film. MS ESI (+) m/z 502 (M+E) detected; 1H NMR (400 MHz, CDCl3) δ 7.52 (m, 1H), 7.46 (d, J=8.0H7-2H), 7.37 (m, 2H), 7.30 (m, 1H), 7.10 (m, 2H), 5.70 (m, 1h), 3.79 (s, 3H), 3.40 (m, 3H), 3.16 (m, 1H), 3.14 (s, 3H), 2.85 (s, 3H), 2.45 (m, 1H), 2.10 (m, 1H).

Provenance & Evidence