Isobutyric Acid → HCID 66673600, compound

Participants

Reaction Steps

TBTU (279 mg, 0.87 mmol) and HOBT (24 mg, 0.17 mmol) were added to a mixture of 2-methylpropanoic acid (81 μL, 0.87 mmol), diisopropylethylamine (0.758 mL, 4.35 mmol) in DMF (5 mL) at ambient temperature. The mixture was stirred at ambient temperature for 15 min. The mixture was charged with 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbohydrazide (352 mg, 0.87 mmol), and was stirred at ambient temperature overnight. The mixture was charged with water and set at ambient temperature overnight. The resulting tan precipitate was filtered, washed with water, and dried in a vacuum oven to give 350 mg (85%) of N′-(2-methylpropanoyl)-4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbohydrazide as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 9.31 (d, 1H, J=1.9 Hz), 8.44 (d, 1H, J=2.9 Hz), 8.36 (d, 1H, J=1.9 Hz), 8.29 (d, 2H, J=8.6 Hz), 8.06 (d, 1H, J=8.8 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.55 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 4.08-3.96 (m, 4H), 3.25 (s, 3H), 2.80-2.70 (m, 2H), 2.41 (septet, 1H, J=6.8 Hz), 2.08-1.92 (m, 1H), 1.82-1.73 (m, 2H), 1.30-1.10 (m, 2H), 1.02 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 475 (M+H).

Provenance & Evidence