Trifluoroacetic acid → HCID 67347140, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-(2-(7-(4-(1-(carbamoyl)cyclopropanecarboxamido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)ethynyl)piperidine-1-carboxylate (Example 124, Step B, 20 mg, 0.0297 mmol) and 2,2,2-trifluoroacetic acid (339 mg, 2.97 mmol) were stirred at room temperature for 30 minutes. The reaction was concentrated in vacuo, using toluene to azeotrope (3×5 mL). The residue was partioned between EtOAc (5 mL) and 1:1 water/saturated aqueous NaHCO3 (5 mL). The phases were separated and the aqueous phase was re-extracted with EtOAc (2×5 mL). The combined organic phases were washed with brine (5 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by preparative TLC (0.5 mm thickness, Rf=0.22), eluting with 10% MeOH (containing 7N NH3) in CHCl3. The product was obtained as a beige powder (10 mg, 55%). HPLC: 93% purity (220 nm); LRMS (APCI+): 94% purity, 220 nm, m/z 573 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 10.07 (s, 1H), 8.47 (d, J=6 Hz, 1H), 8.30 (s, 1H), 7.76 (m, 1H), 7.52 (s, 1H), 7.44 (m, 2H), 7.24 (m, 2H), 7.06 (t, J=9 Hz, 2H), 6.51 (d, J=6 Hz, 1H), 3.12 (m, 3H), 2.79 (m, 3H), 2.00 (m, 2H), 1.80 (m, 4H), 1.62 (m, 2H).

Provenance & Evidence