1,2-Dichloroethane → HCID 59143428, compound

Participants

Reaction Steps

4-Tetrahydropyran-carboxylic acid (66 mg; 0.50 mmol; 1.1 equiv.), HOBt (81 mg; 0.6 mmol; 1.4 equiv.) and EDC (115 mg; 0.6 mmol; 1.4 equiv.) were combined in 2 mL anhydrous DMF. After 15 minutes [1,4]Diazepane-1-carboxylic acid (3-sec-butyl-isoxazol-5-yl)-amide from above (117 mg; 0.44 mmol; 1.0 equiv.) was added, followed by 2 mg of DMAP (catalytic). The mixture was left stirring overnight. Water was added to the reaction mixture and it was extracted with EtOAc. The organic layer was washed with water once then saturated aqueous NaHCO3 solution, saturated aqueous NH4Cl solution, then brine. The organics were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography using 2.5% MeOH/DCM mixtures as eluent, then switched to 10% MeOH/DCM. Solvents were removed from the enriched fractions and 61 mg of 4-(Tetrahydro-pyran-4-carbonyl)-[1,4]diazepane-1-carboxylic acid (3-sec-butyl-isoxazol-5-yl)-amide was obtained (36% yield) as a light yellow solid.

Provenance & Evidence