HCID 86758720, compound → HCID 18342548, compound

Participants

Reaction Steps

A solution of 2-(R)-(3-(S)-((4-(N-(prop-1-yl)-N-(pyrimid-2-yl)amino)-piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)cyclohexylacetic acid, benzyl ester (80 mg, 0.13 mmol) from Example 25 Step A, in 3.0 mL of MeOH was hydrogenated using 10% palladium on carbon (20 mg, 0.026 mmol) under one atmosphere of hydrogen gas. After TLC indicated the absence of the starting benzyl ester, the reaction was filtered through a 0.45 micron nylon membrane polypropylene filter and concentrated under reduced pressure to give 60 mg (80%) of the title compound as a white solid. HPLC (Zorbax SB-C8 column, 4.6 mm×7.5 cm, Gradient: 90 H2O:10 CH3CN to 0 H2O:100 CH3CN over 7.5 minutes then hold at 100 CH3CN:0 H2O for 45 seconds, 2.25 mL/min, 220 nm): Retention Time: 3.4 minutes. ESI-MS: 538.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 0.89-0.92 (t, J=7.4 Hz, 3H), 1.20-3.42 (25H), 3.87 (1H), 4.59 (1H), 6.42-6.43 (t, J=4.8 Hz, 1H), 6.91-6.95 (t, J=6.4 Hz, 1H), 7.03-7.09 (m, 2H), 7.24-7.31 (m, 1H), 8.24-8.25 (d, J=4.6 Hz, 2H).

Provenance & Evidence