Hydrochloric Acid → 4-(2-(5-((Tert-butoxycarbonyl(methyl)amino)methyl)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid

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Reaction Conditions

Reaction Steps

A solution of methyl 4-(2-(5-((tert-butoxycarbonyl(methyl)amino)methyl)pyridine-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinate (2.56 g, 5.06 mmol) in THF (100 mL) was treated with NaOH 5N (6 eq, 30.4 mmol, 6 mL) and stirred at 23° C. for 10 min. Water (10 mL) was added to the mixture which was them stirred at 23° C. for 2 hours. The mixture was then acidified with HCl conc. to pH 4. Water was added and the aqueous phase was extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to give the crude title material (2.59 g) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.41 (9H, s), 2.75 (3H, s), 4.33 (2H, s), 7.04-7.18 (2H, m) 7.66 (1H, d, J=7.33 Hz) 7.84 (1H, s) 8.20 (1H, d, J=1.52 Hz) 8.30 (1H, d, J=4.80 Hz) 11.92 (1H, s). LC/MS (M+H)+: 492. Ret. time: 1.308 min. (Condition B).

Provenance & Evidence