1,2-Dichloroethane → HCID 46940410, compound

Participants

Reaction Steps

Compound (14-1) (20 mg, 0.042 mmol, 1.0 eq), HOBt (11 mg, 0.084 mmol, 2.0 eq), EDC (HCl salt, 12 mg, 0.063 mmol, 1.5 eq) and diisopropylethylamine (22 μL, 0.13 mmol, 3.0 eq) were dissolved in DMF (400 μL, anhydrous) and CH2Cl2 (400 μL, anhydrous). To this solution was added aniline (19 mg, 0.21 mmol, 5.0 eq) and the reaction stirred at room temperature for 16 hours. After that time water was added and the mixture extracted with CHCl3 (×3). The combined organic phases were dried with brine and Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel chromatography by eluting with a gradient of CHCl3 to [CHCl3/MeOH/NH4OH 90:10:1]. The resulting solid was then dissolved in MeOH, added TFA (100 μL), and purified by reverse-phase chromatography (Solvent A H2O/CH3CN/TFA (95:5:0.05), Solvent B CH3CN/H2O/TFA (95:5:0.05)) with a gradient of 5% to 60% B over 5 minutes to give Compound (15-1)

Provenance & Evidence