Acetyl chloride → HCID 57528914, compound

Participants

Reaction Steps

To a solution of DMAP (1.0 mg) and acetyl chloride (9.3 mg, 0.12 mmol) in 1 mL dichloromethane was added a solution of ethyl ((1S)-5-{2-[2-(3-aminophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate (25 mg, 0.06 mmol) in dichloromethane (1 mL). Then, triethylamine (0.5 mL) was added and the reaction mixture was stirred for 16 h. The reaction mixture was concentrated under reduced pressure and redissolved in acetonitrile/methanol. The solution was filtered through a C8-Silica plug before preparative HPLC purification using 10 to 80% acetonitrile in water gradient to afford 15.3 mg (55.6%) of the desired product. 1H NMR (300 MHz/CDCl3) δ 7.97 (s, 1H), 7.70 (d, 2H), 7.49 (s, 1H), 7.37 (t, 1H), 7.03 (d, 1H), 6.76 (s, 1H), 6.69 (d, 1H), 4.11-4.22 (m, 4H), 3.48 (qr, 1H), 2.92 (t, 2H), 2.72-2.88 (m, 2H), 2.68 (dd, 1H), 2.27-2.40 (m, 5H), 2.16 (s, 3H), 1.64-1.76 (m, 1H), 1.24 (t, 3H). EI-LCMS(rel abundance), m/z 463.4 (MH+, 100%).

Provenance & Evidence