Sodium Hydroxide → HCID 54673430, compound

Participants

Reaction Steps

A solution of 1-(5-(5-chloro-2-(4-(pyrrolidin-1-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 8C) (1.81 g, 2.92 mmol) in methanol (19.49 mL) and aqueous 2N sodium hydroxide (5.85 ml, 11.69 mmol) was heated to 70° C. for 1 hour. The methanol was removed under reduced pressure, and the remaining aqueous layer was diluted with 20 mL water. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with a 2:1 methanol:water solution to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.55 (s, 1H), 8.32 (s, 1H), 8.26 (s, 1H), 7.98-7.91 (m, 2H), 7.43-7.36 (m, 2H), 7.03 (s, 1H), 6.67 (s, 1H), 3.60 (s, 2H), 2.69-2.55 (m, 2H), 2.47-2.33 (m, 6H), 2.04-1.89 (m, 2H), 1.75-1.66 (m, 4H); MS ESI(+) m/z 465.2 [M+H]+.

Provenance & Evidence