Acetyl chloride → (R)-10-(1-acetyl-3-methyl-azetidin-3-yl)-1-methyl-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one

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Reaction Steps

To a mixture of (R)-1-methyl-10-(3-methyl-azetidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one hydrochloric acid (Example #148, 0.4 g, 1.2 mmol) in DCM (15 mL) was added acetyl chloride (0.42 g, 5.35 mmol) and TEA (0.37 g, 3.69 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 1 h. The mixture was concentrated in vacuo and the residue was purified by prep-HPLC (Table 3, Method 29) to give (R)-10-(1-acetyl-3-methyl-azetidin-3-yl)-1-methyl-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one (0.146 g, 11%) as a pale yellow solid. 1H NMR (400 MHz, methanol-d4): δ 7.27 (s, 1H), 7.21 (s, 1H), 6.87 (d, J=10.8 Hz, 1H), 6.45 (s, 1H), 5.04 (m, 1H), 4.90 (m, 1H), 4.61 (m, 4H), 4.34 (m, 1H), 2.04 (m, 3H), 1.79 (m, 3H), 1.44 (m, 3H). LC/MS (Table 1, Method 4) Rt=1.836 min.; MS m/z: 368 [M+H]+.

Provenance & Evidence