Trifluoroacetic acid → HCID 66785035, compound

Participants

Reaction Steps

Compound 28A (0.293 mmol max, crude oil) was added to a 10 mL round-bottomed flask equipped for stirring under nitrogen and dissolved in CH2Cl2(2 mL). Trifluoroacetic acid (2 mL) was then added and the solution was stirred at room temperature for 2 hr. The solvent was removed in-vacuo affording a clear colored oil. This oil was re-dissolved in DMF (3 mL) and piperidine (0.500 mL) and allowed to stir at room temperature for 3 hr. This reaction solution was then directly purified by preparative LC/MS (5-50% CH3CN in H2O). The resultant fractions were collected and the solvent was removed in-vacuo affording a clear colored oil. This oil was re-dissolved in CH3CN (1 mL) and water (2 mL). The resultant solution was frozen and lyophilized to afford 3-amino-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-3-(piperidin-4-yl)propan-1-one (94) as its bis-trifluoroacetic acid salt and as a clear oil (0.176 mmol, 0.118 g, 60% yield over 3-steps). ESI-MS: m/z 428.5 (M+H)+.

Provenance & Evidence