Potassium Phosphate, Tribasic → Methyl 3-fluoro-4-(2-(5-(hydroxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate

Participants

Reaction Conditions

Reaction Steps

(6-(5-Thiocyanatothiazol-2-ylamino)pyridin-3-yl)methanol (1.0 g, 3.78 mmol) was dissolved in methanol (30 mL) and treated with dithiothreitol (0.582 g, 3.78 mmol). The reaction was stirred at 23° C. for 1 hour. DMF (30 mL) was then added, followed by K3PO4 (0.321 g, 1.51 mmol) and methyl 4-chloro-3-fluoropicolinate (0.788 g, 4.16 mmol). The reaction was stirred at 23° C. for 1 hour, then methanol was evaporated. The title material was precipitated by adding water (˜150 mL), collected by filtration and dried under high vacuum to give the title material (1.287 g, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 3.34 (2H, s), 4.46 (2H, d, J=5.05 Hz) 5.22 (1H, t, J=5.56 Hz), 7.10 (1H, d, J=8.34 Hz), 7.15 (1H, t, J=5.31 Hz), 7.74 (1H, dd, J=8.59, 2.27 Hz), 7.84 (1H, s), 8.24 (1H, d, J=1.52 Hz), 8.33 (1H, d, J=5.05 Hz), 11.89 (1H, s). LC/MS (M+H)+: 393. HPLC ret. time (Condition N): 4.319 min.

Provenance & Evidence