HCID 58046450, compound → HCID 67122893, compound

Participants

Reaction Steps

5-Chloro-4-(imidazo[1,2-b]pyridazin-3-yl)-1,3-thiazole-2-carbonyl chloride (59.5 mg, 0.199 mmol) and tert-butyl[(1S,2R)-2-amino-3,3-difluorocyclohexyl]carbamate (54.8 mg, 0.219 mmol) were dissolved in dry dichloromethane (3 mL). The reaction mixture was left to stir at room temperature for 42 h. After consumption of the starting material, trifluoroacetic acid (2 mL) was added to the reaction mixture and left to stir at room temperature for 2 h. The solution was then concentrated and the residue purified by prep HPLC. The compound was neutralized by taking the fractions and adding an aqueous saturated sodium bicarbonate solution and extracting three times with ethyl acetate. The combined organics were dried with magnesium sulfate, filtered, and concentrated to afford the title compound as a yellow solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.73 (d, 1H); 8.66 (s, 1H); 8.24 (d, 1H); 7.45 (dd, 1H); 4.05 (m, 1H); 2.85 (m, 1H); 2.08 (m, 1H); 1.22-2.08 (m, 6H). LRMS (APCI) calc'd for (C16H15ClF2N6OS) [M+H]+, 413.1. found 413.0.

Provenance & Evidence