Hydrochloric Acid → HCID 59392685, compound

Participants

Reaction Conditions

Reaction Steps

A 1.25 M solution of HCl in EtOH (5 ml, 6.26 mmol) is added to 4-{4-[8-(3,5-Difluoro-4-morpholin-4-ylmethyl-phenyl)-quinoxalin-2-yl]-5-methyl-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (Example 121, 239 mg, 0.368 mmol) and the reaction mixture is heated at 60° C. for 4 h. After cooling, the yellow suspension is concentrated under vacuo and the residue is diluted with EtOAc, poured onto a saturated solution of NaHCO3 and extracted 3× with EtOAc. The combined organic layers are washed with NaHCO3, brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is dissolved in CH2Cl2 and purified by chromatography on a 40 g silica gel column on a Combiflash Companion™ (Isco Inc.) apparatus (gradient CH2Cl2/(CH2Cl2:EtOH:NH3 85:13.5:1.5) from 1:0=>1:9) to afford the title compound as a pale orange foam. Rt=0.703 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 505 (M+1)+

Provenance & Evidence