5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amide

Participants

Reaction Steps

Route B: The title compound was prepared as outlined in EXAMPLE 1 from 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18) and 2-(S)-amino-3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1-yl)propan-1-one hydrochloride (Preparation 20). The product was purified by chromatography on silica gel eluting with methanol/dichloromethane (1:19) to give the title compound as a pale yellow solid. δH (CD3OD): 1.08–1.19 (0.5H, m), 1.29–1.51 (1.5H, m), 1.54–1.62 (0.5H, m), 1.73–1.84 (1.5H, m), 3.06–3.36 (4H, m), 3.67–3.95 (2.5H, m), 4.03–4.10 (0.5H, m), 5.32 (1H, t), 6.97–7.04 (2H, m), 7.14 (1H, s), 7.26–7.33 (2H, m), 7.66 (1H, s), 8.55 (1H, s); m/z (ES+)=445 [M+H]+; RT=3.27 min.

Provenance & Evidence