5H,7H,8H-pyrano[4,3-b]pyridin-3-amine → (R)-6-Trifluoromethyl-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid (7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-yl)-amide

Participants

Reaction Steps

The compound is prepared in a similar manner as Compound 18 by condensing (R)-6-(trifluoromethyl)-2,3-dihydrobenzo[1,4]dioxine-2-carboxylic acid (38 mg, 0.15 mmol) with 7,8-dihydro-5H-pyrano[4,3-b]pyridin-3-ylamine (42 mg, 0.28 mmol) for 16 hours and purified by semi-preparative HPLC (55-75 gradient) to give the titled amide (52 mg, 89%). m/z=381.1 (M+1)4. HPLC: 9.62 min. 1H NMR (400 MHz; d6-DMSO) δ 10.38 (m, 1H), 8.52 (d, 1H, J=2.3 Hz), 7.77 (d, 1H, J=2.3 Hz), 7.36 (d, 1H, J=2.0 Hz), 7.26-7.22 (m, 2H), 7.09 (d, 1H, J=7.7 Hz), 5.17-5.14 (m, 1H), 4.52-4.49 (m, 2H), 3.95 (t, 2H, J=5.7 Hz), 2.82 (t, 211, J=5.7 Hz).

Provenance & Evidence