Diisopropylethylamine → 2-(2,2,2-Trifluoro-1,1-dimethyl-ethyl)-5,6,7,8-tetrahydro-Quinoline-6-carboxylic acid (7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-amide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-ylamine (36 mg, 0.24 mmol), (S)-2-(1,1,1-trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acid (38 mg, 0.13 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (136 mg, 0.36 mmol) in DMF (1 mL), N,N-diisopropylethylamine (0.1 mL, 0.6 mmol) was added and the reaction was heated at 60° C. for 16 hours. The crude was purified by semi-preparative HPLC (55-75 gradient) to give the titled amide (41 mg, 74%). m/z=420.2 (M+1)+. HPLC: 10.31 min. NMR (400 MHz; d6-DMSO) δ 10.21 (s, 1H), 8.51 (d, 1H, J=2.5 Hz), 7.82 (d, 1H, J=2.3 Hz), 7.56 (d, 1H, J=8.1 Hz), 7.37 (d, 1H, J=8.1 Hz), 4.68 (s, 2H), 3.95 (t, 2H, J=5.9 Hz), 2.97-2.80 (m, 7H), 2.19-2.14 (m, 1H), 1.95-1.85 (m, 1H).

Provenance & Evidence