Diisopropylethylamine → HCID 44556111, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[5-(3-chlorophenyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}benzoic acid (182 mg, 0.499 mmol, 1 equiv), O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (228 mg, 0.600 mmol, 1.20 equiv), and diisopropylethylamine (97 mg, 0.75 mmol, 1.5 equiv) in 1:2 dichloromethane/tetrahydrofuran (5 mL) was added tert-butyl 4-amino-1-piperidine carboxylate (120 mg, 0.60 mmol, 1.2 equiv). The resulting mixture was stirred at 30° C. overnight, filtered, concentrated to give crude product. The crude product was dissolved in 1:1 trifluoroacetic acid/tetrahydrofuran (10 ml) and stirred at room temperature for 2 h. After removal of the solvent, the resulting residue was purified by preparative HPLC to give the desired product (39.5 mg, 17%). 1H NMR (400 MHz, DMSO-d6), δ: 9.98 (s, 1H), 8.24 (s, 1H), 7.94-7.97 (m, 1H), 7.86 (s, 3H), 7.61-7.75 (m, 6H), 7.29-7.32 (m, 3H), 3.30-3.40 (m, 3H), 3.00 (m, 2H), 1.89 (m, 2H), 1.40 (m, 2H). LCMS (ESI) m/z: 447.0.

Provenance & Evidence