Hydrochloric Acid → HCID 58379668, compound

Participants

Reaction Steps

To a solution of tert-butyl (6S)-3-{(1E)-3-[(1R)-2,3-dihydro-1H-inden-1-yl(3-fluoro-2,2-dimethylpropanoyl)amino]prop-1-en-1-yl}-2′-oxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-1′(2′H)-carboxylate (130 mg, 0.213 mmol, described in step F) in DMF (2 mL) was added 1 N aqueous HCl (6.4 mL, 6.39 mmol). The reaction was stirred at ambient temperature and upon completion 1 N aqueous NaOH (4 mL) was added to bring to an approximately neutral pH. The mixture was then partitioned between 5% sodium bicarbonate and DCM. The organics were then washed once with half-saturated brine. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue which still contained a considerable quantity of DMF. This residue was purified by reverse phase HPLC eluting with MeCN/Water (0.1% TFA). The product containing fractions were pooled, and neutralized with 10% NH4OH in MeOH. The bulk of the organics were then removed in vacuo, and the remaining mostly aqueous layer was extracted twice with DCM. The DCM solution was dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title compound. MS: m/z=511 (M+1). Human CGRP receptor binding Ki=0.060 nM. HRMS: m/z=551.2517; calculated m/z=551.2504 for C31H31FN4O2.

Provenance & Evidence