Triethylamine → HCID 24826252, compound

Participants

Reaction Conditions

Reaction Steps

3-(2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)benzoic acid (0.1 g, 0.3055 mmol), triethylamine (0.2129 mL, 1.527 mmol) and THF (2 mL) were combined according to the method of Example 32. The reaction mixture was cooled to 0° C., ethyl carbonochloridate (0.03359 mL, 0.3513 mmol) was added, and the reaction mixture was stirred at 0° C. for 30 minutes. N1,N1-dimethylethane-1,2-diamine (0.1006 mL, 0.9164 mmol) in THF (2 mL) was added to afford N-(2-(dimethylamino)ethyl)-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzamide dihydrochloride (0.07 g, 48.23% yield) as off white solid. 1H NMR (CDCl3) δ 8.97 (bs, 1H), 8.16 (d, 1H), 7.99 (m, 2H), 7.52 (t, 1H), 7.23 (d, 1H), 6.92 (bs, 1H), 6.39 (s, 1H), 3.90 (m, 2H), 3.37 (m, 2H), 2.92 (s, 6H), 2.38 (s, 3H); Mass spectrum (esi) m/z=398 (100) (M+H).

Provenance & Evidence