Sodium Carbonate → 3-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-((4-phenylpiperidin-4-yl)methyl)picolinamide

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)-4-phenylpiperidine-1-carboxylate (˜1.80 g, ˜2.84 mmol, described in Example 1) was dissolved in trifluoroacetic acid/dichloromethane (1:5, mL). This mixture was stirred at 23° C. for 2 hours, then neutralized with sat. sodium carbonate to pH˜7. The aqueous phase was then extracted with ethyl acetate/THF and the combined organic layers were dried over anhydrous magnesium sulfate to give the title material (1.06 g, 70%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.99-2.09 (2H, m), 2.28 (2H, br s), 2.31 (3H, s), 2.66-2.82 (2H, m), 3.25 (2H, m), 3.45 (2H, br d), 6.86 (1H, d, J=5.31 Hz), 6.93 (1H, s), 7.05 (1H, t, J=5.18 Hz), 7.26-7.34 (1H, m), 7.38-7.46 (4H, m), 7.81 (1H, s), 8.17 (1H, d, J=5.31 Hz), 8.23 (1H, d, J=5.05 Hz), 8.37 (1H, t, J=6.44 Hz), 11.84 (1H, s). LC/MS (M+H)+: 535. HPLC ret. time (Condition C): 4.085 min.

Provenance & Evidence