Water → HCID 86615674, compound

Participants

Reaction Steps

To a solution of 0.2 g (0.5 mmol) 3-amino-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[(methylsulfonyl)(propyl)amino]benzamide (Intermediate XXI) in 4 mL acetic acid was added 1 mL water followed by 0.038 g (0.55 mmol) sodium nitrite. After 2 minutes 0.035 g (0.055 mmol) sodium azide was added resulting in gas evolution. The reaction mixture was stirred for 30 minutes then diluted with 75 mL EtOAc, washed with 50 mL water, 50 mL 4M NaOH, 50 mL brine, dried over MgSO4, filtered, and concentrated. Purification by automated flash chromatography (40 g silica gel cartridge, 20-100% EtOAc/hexanes over 20 min) afforded 3-azido-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[(methylsulfonyl)(propyl)amino]benzamide. 1H NMR (CDCl3, 400 MHz) δ 7.45 (br t, J=1.47 Hz, 1H), 7.36 (m, 3H), 7.11 (t, J=2.01 Hz, 1H), 7.06 (m, 2H), 6.31 (br d, J=7.32 Hz, 1H), 5.28 (quint, J=7.14 Hz, 1H), 3.64 (t, J=7.15 Hz, 2H), 2.89 (s, 3H), 1.61 (d, J=6.96 Hz, 3H), 1.5 (m, 2H), 0.91 (t, J=7.33 Hz, 3H). LCMS [M+H]+=420.1

Provenance & Evidence