Trifluoroacetic acid → HCID 178496844, compound

Participants

Reaction Steps

Triethylsilane (0.434 mL, 2.721 mmol) was added to a stirred solution of racemic methyl 7-(5-fluoro-2-(5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-ylamino)bicyclo[3.2.2]nonane-6-carboxylate, 58, (0.365 g, 0.544 mmol) and trifluoroacetic acid (0.419 mL, 5.440 mmol) in dichloromethane (20 mL). The resulting yellow solution was stirred at room temperature for 2 hr and concentrated in vacuo. Water (10 mL) and aqueous saturated NaHCO3 (5 mL) were added and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic phases were dried (MgSO4), filtered and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (10-90% MeOH/CH2Cl2 gradient) to afford 178 mg of the desired product as a white foamy solid: 1H NMR (400 MHz, CDCl3) δ 8.63 (s, 1H), 8.55 (s, 1H), 8.31 (s, 1H), 5.20 (s, 1H), 3.71 (s, 3H), 2.62 (m, 1H), 2.53 (m, 1H), 2.24 (m, 1H), 2.06 (m, 1H), 1.98-1.58 (m, 9H); LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=2.74 minutes (M+H) 329.86.

Provenance & Evidence