Potassium Hydroxide → HCID 71726519, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-N-(8-((2-amino-4-methylpentyl)oxy)-5H-chromeno[3,4-c]pyridin-4-yl)acetamide (20 mg, 0.056 mmol) (prepared as in Example 12, Part H) in a mixture of ethanol (10 mL) and water (2 mL) was added KOH (31.6 mg, 0.563 mmol) and the reaction was heated at 70° C. for 14 h. After completion of the reaction, the volatile organic solvent was removed under reduced pressure, water (20 mL) was added and the solution extracted with dichloromethane (2×20 mL). The combined organic extracts were washed with water (1×20 mL), dried over sodium sulfate and concentrated under reduced pressure to obtain (S)-8-((2-amino-4-methylpentyl)oxy)-5H-chromeno[3,4-c]pyridin-4-amine (2.31 mg, 7.15 umol, 13% yield) as an off-white solid. 1H NMR (400 MHz, MeOD) δ 7.90 (d, J=5.6 Hz, 1 H), 7.69 (d, J=8.7 Hz, 1 H), 6.98 (d, J=5.6 Hz, 1 H), 6.72 (m, 1 H), 6.6 (d, J=2.5 Hz, 1 H), 5.07 (s, 2 H), 4.10 (m, 1 H), 3.92 (m, 1 H), 3.40 (m, 1 H), 1.82 (m, 1 H), 1.49 (m, 2 H), 1.01 (m, 6 H); LCMS (ESI) m/e 314.2 [(M+H)+, calcd for C18H24N3O2 314.2]; LC/MS retention time (Method C): tR=1.21 min; HPLC retention time (method A): tR=7.52 min; HPLC retention time (method B): tR=8.68 min.

Provenance & Evidence