Formaldehyde → HCID 86727508, compound

Participants

Reaction Steps

To a solution of (R)-7-(2-fluoro-phenyl)-4-methyl-6-[(R)-1-(3-methyl-azetidin-3-yl)-ethyl]-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.04 g, 0.098 mmol) in AcOH (0.5 mL) and MeOH (5 mL) was added paraformaldehyde (0.029 g, 0.979 mmol) and the resulting mixture was stirred at ambient temperature for 1 h. NaBH3CN (0.015 g, 0.245 mmol) was added and the reaction mixture was stirred at ambient temperature overnight. Aqueous NaHCO3 (10 mL) was added and the aqueous solution was extracted with EtOAc (3×30 mL). The combined organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo and the residue was purified by prep-HPLC (Table 3, Method 25) to give (R)-6-[(R)-1-(1,3-dimethyl-azetidin-3-yl)-ethyl]-7-(2-fluoro-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.017 g, 40%). 1H NMR (CD3OD, 400 MHz): δ 7.40-7.48 (m, 1H), 7.15-7.32 (m, 3H), 6.91 (s, 1H), 6.84 (s, 1H), 4.83 (m, 1H), 4.58-4.69 (m, 2H), 2.87-3.19 (m, 3H), 2.73-2.87 (m, 2H), 2.10-2.22 (m, 3H), 1.50 (m, 3H), 1.25-1.35 (m, 3H), 1.13-1.23 (m, 3H). LC/MS (Table 1, Method 4) Rt=1.858 min; MS m/z: 423 [M+H]+. SFC (Table 1, Method 15) Rt=1.592 min.

Provenance & Evidence