HCID 66791512, compound → HCID 66784278, compound

Participants

Reaction Steps

tert-Butyl (2R)-4-(3-(6-(hydrox ymethyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-1-(naphthalen-2-yl)-4-oxobutan-2-ylcarbamate (45A) (0.20 mmol, 120 mg) in DCM (10 mL) was added TEA (2 mL). The reaction solution was stirred at rt for 1 hr and then concentrated in vacuo. The residue was purified by preparative LC/MS (5-45% CH3CN in H2O) to afford (3R)-3-amino-1-(3-(6-(hydroxymethyl)-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-(naphthalen-2-yl)butan-1-one (113) (0.016 mmol, 8 mg, two-step yield: 13.3%). ESI-MS: m/z 515.5 (M+H)+. 1H NMR (400 MHz, MeOD) δ ppm 1.56-1.70 (m, 1H) 1.77-2.09 (m, 2H) 1.85-1.86 (m, 3H) 2.12-2.34 (m, 3H) 2.63-3.02 (m, 4H) 3.03-3.11 (m, 2H) 3.13 (d, J=7.26 Hz, 2H) 3.15-3.27 (m, 3H) 3.29 (s, 1H) 3.36-3.51 (m, 3H) 3.67-4.29 (m, 4H) 4.50-4.72 (m, 1H) 7.39-7.44 (m, 2H) 7.49 (ddd, J=9.32, 6.06, 2.81Hz, 3H) 7.56 (d, 0.7=8.65 Hz, 1H) 7.69-7.74 (m, 1H) 7.79-7.94 (m, 3H).

Provenance & Evidence