Diisopropylethylamine → HCID 11511828, compound

Participants

Reaction Steps

A solution of 2,4-Dichloro-N-{1-methyl-1-[4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (V-1, 45 mg, 0.12 mmol) in DMF (1 mL) was cooled in an ice bath and treated with i-Pr2NEt (0.086 mL, 0.49 mmol) followed by azetidinylsulfamoyl chloride (literature reference J. Chem. Soc. Perkin 1 1994, p1595) (29 mg, 0.19 mmol). The mixture was allowed to warm to room temperature and stirred at room temperature for 12 h. The volatile components were removed in vacuo and the residue purified by preparative TLC eluting with 3% methanol-DCM to afford 2,4-dichloro-N-{1-methyl-1-[1-(azetidinesulfonyl)-4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (V-2). 1H NMR (CDCl3, 500 MHz) δ 8.55 (d, J=3.4 Hz, 1H), 7.71 (t, J=7 Hz, 1H), 7.57 (d, J=8 Hz, 1H), 7.37 (m, 2H), 7.27 (m, 1H), 7.19 (m, 1H), 7.08 (s, 1H), 3.90 (t, J=7.5 Hz, 4H), 3.84 (d, J=6.5 Hz, 2H),), 3.46 (m, 2H), 3.30 (m, 2H), 2.31 (m, 2H), 2.22 (m, 2H), 1.94 (m, 2H); MS 483 (M+H).

Provenance & Evidence