Hydrochloric Acid → 1-{5-[5-fluoro-2-(3,4,5-trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,3-thiazol-2-yl}cyclobutanol

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Reaction Steps

1-(5-(5-fluoro-1-tosyl-2-(3,4,5-trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 90A) (103 mg, 0.169 mmol) in methanol (2.50 mL) and 2N aqueous sodium hydroxide solution (830 μL) was heated by microwave irradiation (Biotage, Initiator) to 120° C. for 30 minutes. The reaction was cooled to room temperature, and the pH was adjusted to ˜3 with 10% aqueous HCl solution. The resulting solution was purified by reverse phase high performance liquid chromatography (RP HPLC, eluting with a gradient of 5% B in A to 75% B in A over 25 minutes, wherein A is water containing 0.1% v/v ammonium acetate and B is acetonitrile) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.48 (bs, 1H), 8.80 (s, 1H), 8.29 (d, J=2.0 Hz, 1H), 8.37 (m, 3H), 6.69 (s, 1H), 3.91 (s, 6H), 3.71 (s, 3H), 2.64-2.55 (m, 2H), 2.45-2.35 (m, 2H), 2.05-1.92 (m, 2H); MS ESI(+) m/z 456.1 [M+H]+.

Provenance & Evidence