Glycolic Acid → 1-[4-{6-Amino-7-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydropyridin-1(2H)-yl]-2-hydroxyethanone

Participants

Reaction Steps

A mixture of 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-furo[3,2-c]pyridin-6-ylamine (0.010 g, 0.024 mmol), DIPEA (0.00918 g, 0.071 mmol), TBTU (0.0228 g, 0.071 mmol) in DCM (2 mL) was added Glycolic acid (0.00360 g, 0.0474 mmol) at 0° C. The mixture was stirred for 1 h. The reaction mixture was directly loaded onto Prep TLC for purification (silica gel, eluting with 4% MeOH in DCM) to afford the title compound as a yellow solid. 1H-NMR (CD3OD, 400 MHz): δ=1.88 (d, J=6.8 Hz, 3H), 2.53 (d, J=17.2 Hz, 2H), 3.63 (t, J=5.8 Hz, 1H), 3.83 (t, J=5.8 Hz, 1H), 4.12 (d, J=2.0 Hz, 1H), 4.26 (s, 2H), 4.30 (s, 1H), 6.29 (d, 1H), 6.49 (q, J=6.7 Hz, 1H), 7.15-7.25 (m, 1H), 7.39 (dd, J=9.0, 4.9 Hz, 1H), 7.64 (d, J=10.4 Hz, 1H), 8.20 (s, 1H). MS (ES+): m/z 480.01 (MH+, 35Cl, 37Cl), 481.96 (MH+, 37Cl, 37Cl). HPLC: tR=2.76 min (polar—5 min, ZQ3).

Provenance & Evidence