HCID 68277893, compound → HCID 56960297, compound

Participants

Reaction Steps

2-(bromomethyl)-6-(trifluoromethoxy)benzo[d]thiazole (4.4 g, 0.0141 mol) and N-Me-propargylamine (2.4 g, 2.5 eq, 0.035 mol) were dissolved in acetonitrile (70 ml) and the reaction mixture was heated to reflux for 1 h. Then it was cooled, evaporated to dryness and the residue was partitioned between EtOAc and water (100 ml:100 ml), NH4OH was add (to give pH of 9-10) and the organic phase was separated, dried over Na2SO4, evaporated and the residue purified by chromatography (hexane-EtOAc) to give 4.1 g (97%) of N-methyl-N-((6-(trifluoromethoxy)benzo[d]thiazol-2-yl)methyl)prop-2-yn-1-amine. The free base (4.1 g) was dissolved in 100 ml Et2O and HCl/IPA (2N) was added (pH=1-2). The white suspension that was obtained was filtered and the collected solid was dried to give 2.7 g (mp=117-120° C.) which was identified to be the HCl salt of compound C. 1H-NMR (of the HCl salt of the title compound, DMSOd6) δ 8.38 (s, 1H, Ar), 8.20 (d, 1H, Ar), 7.58 (d, 1H, Ar), 4.86 (br s, 2H, C—CH2) 4.22 (br s, 2H, MeN-CH2—C), 3.88 (s, 1H, CH), 2.89 (s, 3H, NMe); 13C-NMR (DMSOd6) δ 163.38, 150.96, 145.83, 136.87, 124.36, 120.36, 120.08, 115.46, 81.22, 73.60, 53.50, 44.37; LCMS (ES-API for free base) 301.0 (M+H).

Provenance & Evidence