Propargylamine → HCID 56960296, compound

Participants

Reaction Steps

2-(bromomethyl)-6-(trifluoromethoxy)benzo[d]thiazole (3.8 g, 0.0122 mol) and propargylamine (1.7 g, 2.5 eq) were dissolved in acetonitrile (50 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, 0.5 ml of NH4OH was add (pH=9-10) and the organic phase was separated, dried over Na2SO4, evaporated and the residue purified by chromatography (hexane-EtOAc) to give 3 g (86%) of N-((6-(trifluoromethoxy)benzo[d]thiazol-2-yl)methyl)prop-2-yn-1-amine. The free base was dissolved in 100 ml Et2O and HCl/IPA was added. The white suspension that was obtained was filtered and dried to give 2.7 g (mp=188-189° C., dec) of white solid, which was identified as the HCl salt of Compound B. 1H-NMR (of the HCl salt of the title compound, DMSOd6) δ 10.23 (br s, 2H, NH2), 8.35 (s, 1H, Ar), 8.16 (d, 1H, Ar), 7.57 (d, 1H, Ar), 4.76 (s, 2H, C—CH2) 4.04 (d, 2H, N—CH2—C), 3.74 (s, 1H, CH); 13C-NMR (DMSOd6) δ 164.40, 150.66, 145.74, 136.53, 124.01, 120.39, 120.10, 115.54, 79.84, 74.88, 46.05, 35.80; LCMS (ES-API for free base) 287.0 (M+H).

Provenance & Evidence