2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 59239562, compound

Participants

Reaction Steps

Step 1—Synthesis of (S)-6-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-7-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyridin-2-amine (pk). To a solution of (S)-6-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)pyridin-2-amine hydrochloride salt (ms) (51 mg, 0.094 mmol) in Acetonitrile (1.0 mL) and N,N-Diisopropylethylamine (0.10 mL, 0.57 mmol) was added trifluoroethanol triflate (0.020 mL, 0.14 mmol) at room temperature, and the reaction mixture was microwaved at 140° C. for 30 minutes, followed by the addition of a second portion of Trifluoroethanol triflate (0.030 mL, 0.21 mmol). The resultant reaction mixture was microwaved at 140° C. for 20 minutes. The reaction mixture was diluted with Ethyl acetate, and washed by NaHCO3, water, and brine till pH 7. The orange organic solution was evaporated after dried over Magnesium sulfate. The residue was purified on a silica gel column to give the desired product (pk) (61 mg, 110% yield) as yellow powder: 1H NMR (500 MHz, CDCl3) δ 8.30 (d, J=8.4 Hz, 2H), 7.46 (m, 5H), 7.39 (t, J=7.5 Hz, 2H), 7.32 (t, J=7.2 Hz, 1H), 6.55 (s, 1H), 6.45 (d, J=7.8 Hz, 1H), 6.31 (d, J=7.9 Hz, 1H), 5.38 (s, 2H), 4.11 (m, 1H), 4.06-3.80 (m, 4H), 3.80-3.47 (m, 4H), 3.20 (q, J=9.4 Hz, 2H), 3.05-2.95 (m, 1H), 2.86 (m, 1H), 2.82-2.68 (m, 2H), 1.33 (d, J=6.6 Hz, 3H); LC-MS m/z=591 (M+H).

Provenance & Evidence