Trifluoroacetic acid → HCID 86727513, compound

Participants

Reaction Steps

To a solution of 3-methyl-3-[(S)-1-((R)-4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester (diastereomer 2, 0.009 g, 0.019 mmol) in DCM (2 mL) was added TFA (0.5 mL) and the reaction mixture was stirred at ambient temperature for 1.5 h. The solvent was removed in vacuo and the residue was purified by prep-HPLC (Table 3, Method 28) to give (R)-4-methyl-6-[(S)-1-(3-methyl-azetidin-3-yl)-ethyl]-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (Example #147-2, Enantiomer 2, 0.006 g, 84%) as a solid. 1H NMR (CD3OD-d4, 400 MHz): δ 7.35 (s, 1H), 6.9 (s, 1H), 4.95 (m, 1H), 4.7 (d, J=12.0 Hz, 2H), 4.4 (d, J=11.2 Hz, 1H), 4.2 (d, J=11.2 Hz, 1H), 3.65 (t, J=8.4 Hz, 2H), 3.26 (m, 1H), 1.5 (m, 6H), 1.45 (m, 3H). LC/MS (Table 1, Method 5) Rt=2.310 min; MS m/z: 383 [M+H]+. SFC (Table 1, Method 36) Rt=4.712 min.

Provenance & Evidence