3-Aminoquinoline → HCID 66815452, compound

Participants

Reaction Steps

N,N-diisopropylethyl amine (12.1 mL, 69.4 mmol) was added to a solution of 4-tert-butoxycarbonylamino-benzoic acid (9.05 g, 38.1 mmol), quinolin-3-ylamine (5.0 g, 34.7 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospate (HBTU) (14.5 g, 38.1 mmol) in acetonitrile (200 mL) and was stirred at ambient temperature for ten minutes. The solution was heated at reflux for approximately 18 hours. Upon cooling to room temperature, the product crystallized and was collected by filtration, to give a colorless solid, 7.9 g (63%). MS: m/z 364 (MH+). 1H NMR (DMSO-d6): δ 1.51 (s, 9 H), 7.57-7.70 (m, 4 H), 7.75-8.00 (m, 4 H), 8.83 (d, J=2 Hz, 1 H), 9.15 (d, J=2 Hz, 1 H), 9.75 (br s, 1 H) and 10.54 (br s, 1 H).

Provenance & Evidence