Acetic Acid → HCID 18506846, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of tert-butyl 4-acetylpyridin-2-ylcarbamate (16-3, 187 mg, 0.79 mmole) in MeOH (3 mL) was added 1-acetylpiperazine (304 mg, 2.37 mmole), glacial HOAc (0.14 mL, 2.37 mmole), and NaBH3CN (149 mg, 2.37 mmole) then the mixture was heated to 50° C. After 6 hr additional NaBH3CN (149 mg, 2.37 mmole) was added and heating continued. After 18 hr the mixture was cooled to RT, diluted with saturated NaHCO3, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (gradient, 0-10% EtOH/EtOAc) gave the titled compound as an oil: 1H-NMR (500 MHz, CDCl3) δ 8.17 (d, 1 H, J=5.13 Hz), 7.87 (s, 1H), 7.52 (bs, 1 H), 6.97 (d, 1 H, J=5.13 Hz), 3.64-3.57 (m, 2 H), 3.45-3.39 (m, 3 H), 2.49-2.35 (m, 4 H), 2.06 (s, 3 H), 1.54 (s, 9 H), 1.35 (d, 3 H, J=6.59 Hz).

Provenance & Evidence