Reaction Steps
To a stirring suspension of 3-fluoro-N-(2-hydroxy-2-phenylpentyl)-4-(2-(5-(piperidin-4-ylamino)pyridin-2-ylamino)thiazol-5-ylthio)picolinamide (737 mg, 1.021 mmol), dimethylglycine (636 mg, 6.167 mmol), EDAC (590 mg, 3.078 mmol), HOBt (275 mg, 2.035 mmol) in NMP (10 mL) was added i-Pr2Net (1.8 ml, 10.3 mmol). After 2 h, the reaction was diluted with PrepLC solvent B (TFA):TFA (8 mL:2 mL), filtered into 14 prepLC vials, purified on PrepLC (YMC-Pack C18 30×100 mm, NH4Oac). The fractions containing the product were concentrated in SpeedVac overnight. The fractions were pooled together using MeOH and concentrated. The product was obtained (417 mg, 59%) as a solid, then converted to the HCl salt: 1H NMR (400 MHz, DMSO-d6) δ ppm: 11.52 (1H, s), 9.53 (1H, s), 8.23 (2H, t, J=5.81 Hz), 7.78 (1H, s), 7.72 (1H, s), 7.42 (2H, d, J=7.33 Hz), 7.29 (2H, t, J=7.58 Hz), 7.18 (2H, t, J=7.33 Hz), 7.03 (1H, t, J=5.31 Hz), 6.96 (1H, d, J=8.84 Hz), 4.29 (2H, m), 3.61 (3H, d, J=5.81 Hz), 3.15 (1H, m), 2.93 (1H, t, J=11.62 Hz), 2.75-2.82 (6H, m), 1.95 (3H, t, J=9.98 Hz), 1.65-1.78 (2H, m), 1.33 (2H, s), 1.17-1.26 (2H, m), 0.88 (1H, m), 0.74 (3H, t, J=7.20 Hz); LC/MS (M+H)+: 693. HPLC ret. time (Condition M): 1.40 min.
