Trifluoroacetic acid → HCID 89630059, compound

Participants

Reaction Steps

To a solution of crude N-(3-(5-(thiazol-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide (38 mg, 0.076 mmol) in DCM (1.0 mL), was added TFA (1.0 mL). The resulting solution was stirred at room temperature for approximately 3 hours before being concentrated in vacuo. The crude residue was then taken up into MeOH (1.0 mL) and ammonium hydroxide (1.0 mL) was added, and the resulting mixture was stirred at room temperature for approximately 30 minutes. The reaction was concentrated to afford a crude solid that was dissolved in a mixture of MeOH and EtOAc, filtered through 2 Stratospheres™ PL-HCO3 MP SPE cartridges, concentrated in vacuo and purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. Lyophyllization of the desired fractions afforded N-(3-(5-(thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as an off-white solid. LRMS (ESI) calcd for C19H15N5OS [M+H]+: 362, found 362. 1H NMR (600 MHz, DMSO-d6) δ 12.93 (s, 1H), 9.75 (s, 1H), 8.92 (s, 1H), 8.10 (d, J=2.4 Hz, 1H), 7.91 (s, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.55 (m, 2H), 7.07 (t, J=7.8 Hz, 1H), 6.91 (d, J=7.8 Hz, 1H), 5.74 (s, 1H), 5.47 (s, 1H), 1.90 (s, 3H).

Provenance & Evidence