Water → HCID 67774995, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound (ii) (20 mg, 0.029 mmol) and trifluoroacetic acid (50 uL) in DCM (0.5 mL) was stirred at 40° C. for 1 h. After cooling to RT, solid potassium carbonate (50 mg) was added and the mixture was stirred vigorously for 10 min. Water (0.5 mL) was then added and the organic phase was separated. The aqueous phase was extracted with DCM (1 mL) and the combined organics were dried (MgSO4) then concentrated in vacuo. The residue was purified by flash column chromatography eluting with MeOH/DCM (0-20%) to afford Compound (61) as a white solid (5.4 mg, 32%). ESI-MS m/z calculated for [M+H]+: 591.1/593.1; found: 591.1/593.1; 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.69-7.60 (m, 2H), 7.50-7.42 (m, 2H), 7.35 (s, 1H), 7.24 (t, J=4.3 Hz, 1H), 5.95 (brd, J=4.6 Hz, 1H), 3.92-3.68 (m, 2H), 3.46-3.22 (m, 2H), 3.06 (s, 3H), 3.02-2.90 (m, 5H), 2.38 (tt, J=8.4, 5.4 Hz, 1H), 2.31-2.16 (m, 2H), 1.92-1.68 (m, 2H), 1.12-0.96 (m, 3H), 0.67-0.54 (m, 1H).

Provenance & Evidence