Hydrochloric Acid → HCID 24826144, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)benzoic acid (0.100 g, 0.2912 mmol) and THF (30 mL) and cooled to −5° C. Triethylamine (0.08840 g, 0.8736 mmol) and ethyl carbonochloridate (0.02784 mL, 0.2912 mmol) were added successively. The reaction mixture was stirred at −5° C. for 30 minutes. N1,N1-dimethylethane-1,2-diamine (0.07701 g, 0.8736 mmol) was added and stirred at −5° C. for 30 minutes and room temperature for 1 hour. An aqueous workup was done, the organic layer was dried and concentrated, and the residue was purified by silica gel chromatography to give the free base. The free base was dissolved in DCM, and 2M HCl was added. The solution was concentrated to provide N-(2-(dimethylamino)ethyl)-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)benzamide dihydrochloride (0.060 g, 42.36% yield). 1H NMR (d6-DMSO) δ 11.34 (bs, 1H), 9.97 (bs, 1H), 8.94 (t, 1H), 8.13 (m, 2H), 8.07 (d, 1H), 7.79 (d, 1H), 7.67 (t, 1H), 6.80 (s, 1H), 6.66 (s, 1H), 6.58 (s, 1H), 3.63 (m, 2H), 2.26 (m, 2H), 2.82 (d, 6H), 2.21 (s, 3H); Mass spectrum (apci) m/z=414.0 (M+H-2HCl).

Provenance & Evidence