1-Hydroxybenzotriazole → HCID 118092837, compound

Participants

Reaction Steps

Piperazin-2-one (80.0 mg, 0.801 mmol), silica-bound carbodiimide (1.08 mmol/g load, 989 mg, 1.07 mmol), and HOBT (123 mg, 0.801 mmol) were added to a solution of 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxylic acid (200 mg, 0.534 mmol) in DMF (5.30 mL) and the reaction mixture was stirred at room temperature overnight. Macroporous-carbonate (3.17 mmol/g load, 1.01 g, 3.21 mmol) was added to the reaction mixture and stirred overnight at room temperature. The reaction mixture was filtered, washed with DMF and was concentrated under reduced pressure. The residue was triturated with dichloromethane and was isolated by filtration (cold ether wash) to yield 4-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]carbonyl}piperazin-2-one. MS APCI calc'd for C22H20F3N6O2 [M+H]+ 457. found 457. 1H NMR (500 MHz, DMSO-d6) δ 10.30 (s, 1H), 8.84 (d, J=5.5 Hz, 2H), 8.14 (s, 2H), 8.00 (s, 1H), 7.76 (t, 1H), 7.60 (s, 1H), 7.32-7.13 (m, 2H), 4.16 (d, J=12.2 Hz, 2H), 3.92-3.77 (m, 1H), 3.72 (s, 1H), 2.37 (s, 3H).

Provenance & Evidence