Triethylamine → HCID 67436848, compound

Participants

Reaction Conditions

Reaction Steps

Trans-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarboxylic acid (35 mg, 0.16 mmol) was dissolved in SOCl2 (2 mL) and was heated at 65° C. for 3 hrs. Removal of SOCl2 carefully under pump and dried the residue under high vacuum for 3 hrs. To a solution of {(1S,2S)-1-[(6-cyclopropyl-naphthalen-2-ylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (55 mg, 0.14 mmol) and triethylamine (0.084 mL, 0.6 mmol) in DCM (3 mL) at 0° C. was added freshly made trans-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarbonyl chloride in DCM (2 mL) slowly. The reaction mixture was then stirred at r.t. for 18 hrs. The reaction mixture was transferred to a separatory funnel containing water (20 mL). The aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered and concentrated. The residue was purified by Prep HPLC to afford [(1S,2S)-1-({(6-cyclopropyl-naphthalen-2-yl)-[trans-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-amino}-methyl)-2-methyl-butyl]-carbamic acid tert-butyl ester as a solid: LC/MS (ESI) m/e 546 [(M+H)+, calcd for C33H40FN3O3 545.7].

Provenance & Evidence