1,2-Dichloroethane → HCID 25191867, compound

Participants

Reaction Steps

To the suspension of (R)-2-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid (95 mg, 0.23 mmol), (prepared according to example 4) in THF (2.5 mL) at room temperature are added 0.5 M NH3 in 1,4-dioxane solution (0.91 mL, 0.45 mmol) and HOBt (15 mg, 0.11 mmol). Then EDC (87 mg, 0.45 mmol) is added in small portions. The reaction mixture is stirred for 16 hours and then DMF (1.0 mL) along with another 0.5 M NH3 (1.0 mL) in 1,4-dioxane solution and EDC (87 mg, 0.45 mmol) are added. The reaction is continued for another 60 hours. Then water (55 mL) is added and the mixture is extracted with EtOAc (3×30 mL). The organic layers are combined, dried over Na2SO4 and are concentrated to give crude product. Purification by flash column chromatography using 6% MeOH in DCM followed by washing using Methanol affords the title compound. LCMS (ESMS): m/z 419.77 (M+H+).

Provenance & Evidence