Ammonium Chloride → HCID 178504673, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbonitrile (241 mg, 0.65 mmol) in DMF (3 mL) was treated with ammonium chloride (52 mg, 0.97 mmol) and sodium azide (63 mg, 0.97 mmol) at room temperature. The mixture was heated at 100° C. for 19 h. After cooling down, the solid was removed by filtration and washed with DMF. The filtrate was concentrated and a small amount of MeOH and CH2Cl2 was added to the residue. After sonication, the resulting precipitate was collected and washed with THF including a small amount of water. 2-[4-(Methylsulfonyl)phenyl]-5-({[1-(1H-tetrazol-5-yl)-4-piperidinyl]methyl}oxy)pyridine was obtained as a light gray solid (170 mg, 60%) after drying in vacuo. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H, J=2.9 Hz), 8.28 (d, 2H, J=8.6 Hz), 8.07 (d, 1H, J=8.8 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.55 (dd, 1H, Ja=8.8 Hz, Jb=2.9 Hz), 4.03 (d, 2H, J=6.3 Hz), 3.88 (d, 2H, J=12.7 Hz), 3.25 (s, 3H), 3.13-3.00 (m, 2H), 2.13-2.01 (m, 1H), 1.93-1.84 (m, 2H), 1.47-1.31 (m, 2H); LRMS (ESI), m/z 415 (M+H).

Provenance & Evidence