Trifluoroacetic acid → HCID 67441034, compound

Participants

Reaction Steps

To a solution of 246 (722 mg, 0.18 mmol) in DCM (30 mL) was added TFA (7 mL) and the reaction mixture was stirred for 45 min. The reaction mixture was concentrated, diluted with water and 4M NaOH to pH 11 and extracted with AcOEt. The extract was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Biotage (SNAP 50 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 0/100 to 15/85 over 20 CV), to produce a material that upon trituration with AcOEt, afforded the title compound 247 (3.15 mg, 0.617 mmol, 52% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.44 (d, J=5.6 Hz, 1H), 8.33 (s, 1H), 8.01 (d, J=0.8 Hz, 1H), 7.72 (d, J=2.4 and 13.6 Hz, 1H), 7.68 (s, 1H), 7.35 (t, J=9.2 Hz, 1H), 7.22-7.16 (m, 1H), 6.57 (d, J=2.4 Hz, 1H), 6.53 (d, J=5.6 Hz, 1H), 4.21 (t, J=6.0 Hz, 2H), 3.36 (t, J=5.6 Hz, 2H), 2.98 (s, 3H), 2.97 (t, J=6.0 Hz, 2H), 2.68 (t, J=5.6 Hz, 2H), 2.59-2.50 (m, 1H), 0.68-0.62 (m, 2H), 0.45-0.40 (m, 2H). MS (m/z): 511.54 (M+H).

Provenance & Evidence