Reaction Steps
The enantiomers of 1-(1-(4-fluorophenyl)-2-methoxyethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (40 mg, 0.11 mmol) were separated by SFC (Berger Multigram II SFC, column: Phenomenex Lux 4 2.1×25 cm, 5 uM, mobile phase: 30% to 70% MeOH in CO2(l), flow rate: 70 mL/min, 6.5 min run time). The fractions were collected and the solvent evaporated in vacuo to afford 1-[(1R)-1-(4-fluorophenyl)-2-methoxyethyl]-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea and 1-[(1S)-1-(4-fluorophenyl)-2-methoxyethyl]-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea. MS ESI calc'd. For C17H18FN5O3 [M+1]+ 360. found 360. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 9.08 (s, 1H), 8.55 (s, 1H), 7.98 (br s, 1H), 7.47 (s, 1H), 7.36 (dd, J=8.5, 5.5 Hz, 2H), 7.15 (t, J=9.0 Hz, 2H), 4.98-4.92 (m, 1H), 3.96 (s, 3H), 3.55 (d, J=5.0 Hz, 2H), 3.25 (s, 3H) (Example 54). MS ESI calc'd. For C17H18FN5O3 [M+1]+ 360. found 360. 1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 9.08 (s, 1H), 8.55 (s, 1H), 7.98 (br s, 1H), 7.47 (s, 1H), 7.36 (dd, J=8.5, 5.5 Hz, 2H), 7.15 (t, J=9.0 Hz, 2H), 4.98-4.92 (m, 1H), 3.96 (s, 3H), 3.55 (d, J=5.0 Hz, 2H), 3.25 (s, 3H) (Example 55).
