Triethylamine → HCID 86639669, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with 2-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)acetic acid (prepared according to Example 24; 0.050 g, 0.1465 mmol) and THF (30 mL) and cooled to −5° C. Triethylamine (0.03112 g, 0.3076 mmol) and ethyl carbonochloridate (0.07002 mL, 0.7323 mmol) were added successively, and the reaction mixture was stirred at −5° C. for 30 minutes. 1-Methylpiperazine (0.07335 g, 0.7323 mmol) was added, and the reaction mixture was stirred at −5° C. for 30 minutes and then at room temperature for 1 hour. The reaction mixture was washed with water, the organic layer was separated, dried and concentrated, and the residue was purified first by silica gel chromatography and then by reverse phase chromatography to give the title compound as the free base. The free base was dissolved in dichloromethane, and 2M HCl in ether was added. The mixture was concentrated to provide 2-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)-1-(4-methylpiperazin-1-yl)ethanone dihydrochloride (0.024 g, 33.01% yield). 1H NMR (DMSO-d6) δ 10.35 (bs, 1H), 10.11 (bs, 1H), 7.89 (dd, 1H), 7.57 (m, 2H), 7.42 (m, 3H), 7.35 (m, 1H), 6.95 (m, 1H), 6.81 (s, 1H), 5.28 (s, 2H), 4.45 (m, 1H), 4.21 (m, 1H), 3.79 (s, 2H), 3.41 (m, 3H), 2.98 (m, 3H), 2.78 (d, 3H). Mass spectrum (apci) m/z=424.2 (M+H-2HCl).

Provenance & Evidence