Reaction Steps
The enantiomers of 1-((S)-2-Methoxy-1-phenylethyl)-3-(3-(2-methylmorpholino)-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (38 mg, 0.072 mmol) were separated by SFC (Berger Multigram II SFC, column: Chiral Technology IC-H 2.1×25 cm, 5 uM, mobile phase: 39% to 61% MeOH+0.25% dimethyl ethylamine in CO2(1), flow rate: 70 mL/min, 6 min run time). The fractions were collected and the solvent evaporated in vacuo to afford 1-[(1S)-2-methoxy-1-phenylethyl]-3-{3-[(2R)-2-methylmorpholin-4-yl]-1H-pyrazolo[4,3-c]pyridin-6-yl}urea (9.91 mg, 0.024 mmol, 67%) and 1-[(1S)-2-methoxy-1-phenylethyl]-3-{3-[(2S)-2-methylmorpholin-4-yl]-1H-pyrazolo[4,3-c]pyridin-6-yl}urea. MS ESI calc'd. For C21H26N6O3 [M+1]+ 411. found 411. 1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 9.09 (s, 1H), 8.82 (s, 1H), 8.09 (br s, 1H), 7.39 (s, 1H), 7.35-7.31 (m, 4H), 7.26-7.21 (m, 1H), 5.00-4.93 (m, 1H), 3.91-3.83 (m, 1H), 3.78 (d, J=12.0 Hz, 1H), 3.74-3.65 (m, 3H), 3.55 (d, J=5.4 Hz, 2H), 3.25 (s, 3H), 2.91-2.82 (m, 1H), 2.59-2.51 (m, 1H), 1.15 (d, J=6.2 Hz, 3H) (Example 39). MS ESI calc'd. For C21H26N6O3 [M+1]+ 411. found 411. 1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 9.35-9.16 (br s, 1H), 9.11 (s, 1H), 8.83 (s, 1H), 8.18-8.09 (br s, 1H), 7.38 (s, 1H), 7.35-7.29 (m, 4H), 7.27-7.20 (m, 8.7, 1H), 5.02-4.90 (m, 1H), 3.93-3.83 (m, 1H), 3.78 (d, J=11.8 Hz, 1H), 3.74-3.64 (m, 3H), 3.55 (d, J=5.4 Hz, 2H), 3.25 (s, 3H), 3.10-3.01 (m, 1H), 2.93-2.82 (m, 1H), 2.60-2.51 (m, 1H), 1.14 (d, J=6.0 Hz, 3H) (Example 40).
