Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

A flask containing the title compound from Example 1 Step B (20 mg, 0.08 mmol), formic hydrazide (6.0 mg, 0.10 mmol) and cyclohexanol (0.50 ml, 0.08 mmol) was heated to reflux for 6 hours. The reaction was cooled to room temperature, diluted with dimethylsulfoxide, acidified with trifluoroacetic acid and passed through a syringe filter. Purification by reverse phase HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid) provided the title compound: LCMS m/z 249.16 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 9.90 (s, 1H), 9.30 (d, J=2.0 Hz, 1H), 9.01 (ddd, J=1.5, 1.9, 8.2 Hz, 1H), 8.93 (d, J=5.6 Hz, 1H), 8.23 (dd, J=5.8, 8.2 Hz, 1H), 8.10-8.07 (m, 2H), 8.02 (dd, J=1.9, 8.4 Hz, 1H), 3.46-3.43 (m, 2H), 3.38-3.35 (m, 2H).

Provenance & Evidence