Trifluoroacetic acid → HCID 59232091, compound

Participants

Reaction Steps

A suspension of Example 270 (930 mg, 1.5 mmol) in 60 mL 1,2-dichloroethane was treated with 15 mL TFA at rt. The reaction quickly became homogeneous and at 10 min no starting material remained by RP-HPLC. The reaction mixture was concentrated in vacuo, and the residue taken up again in fresh 1,2-dichloroethane and concentrated again; this was repeated 2 times. The residue was taken up in THF (15 mL) and EtOAc (85 mL) and washed with aq. sodium carbonate. The organic layer was dried with sodium sulfate and concentrated in vacuo to provide a tan solid. Trituration with ethyl acetate provided the title compound (705 mg, 91%) as a tan solid. 1H-NMR (DMSO-d6) δ 10.14 (bs, 1H), 10.06 (bs, 1H), 8.54 (d, 1H), 8.26 (t, 1H), 8.01 (s, 1H), 7.88 (s, 1H), 7.31-7.40 (m, 2H), 7.24 (dd, 1H), 6.65 (s, 1H), 3.18 (tt, 1H), 3.01 (broad d, 2H), 2.61 (td, 2H), 1.92 (broad d, 2H), 1.54 (ddd, 2H); MS [M+H]+=515.2; LCMS RT=2.34.

Provenance & Evidence