Trifluoroacetic acid → HCID 11538025, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of compound 365 (19 mg, 0.56 mmol) in DCM 500 μL was added trifluoroacetic acid (200 μL). The solution was refluxed at 50° C. for 3 h and concentrated in vacuo to produce a white solid. This material was dissolved in DMF (500 μL) and was treated with Et3N (16 μL, 0.118 mmol) and BOP (30 mg, 0.067 mmol). The reaction mixture was stirred for 10 min. and 1,2-henylenediamine (7 mg, 0.061 mmol) and another portion of Et3N (23 μL, 0.168 mmol) were added. The mixture was stirred for 2 h at room temperature and DMF was removed in vacuo at 80° C. The residue was partitioned between EtOAc and H2O. The organic layer was collected and extracted with 1N HCl and neutralized with sat. NaHCO3. A precipitate formed which was extracted with EtOAc, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography using MeOH/CHCl3 (7:93) as the eluent to afford the title compound (11 mg, 52% yield). 1H NMR: (CD3OD) δ(ppm): 7.97 (d, J=2.7 Hz, 1H), 7.86 (d, J=8.8 Hz, 2H), 7.78 (dd, J=4.7, 1.0 Hz, 1H), 7.18-7.10 (m, 3H), 7.05 (td, J=7.4, 0.6 Hz, 1H), 6.89 (dd, J=7.8, 1.2 Hz, 1H), 6.76 (td, J=7.4, 1.4 Hz, 1H), 6.64 (d, J=8.8 Hz, 2H), 4.25 (quint, J=4.9 Hz, 1H), 3.77 (dd, J=10.2, 6.1 Hz, 1H), 3.57 (dd, J=17.0, 7.0 Hz, 1H), 3.49 (td, J=8.0, 5.3 Hz, 1H), 3.29 (q, J=6.7 Hz, 1H), 2.41 (sext, J=7.2 Hz, 1H), 2.10 (sext, J=4.9 Hz, 1H). m/z: 372.4 (MH+).

Provenance & Evidence