4-Methylmorpholine → HCID 10288850, compound

Participants

Reaction Steps

N-[(1R,2R)-1-Amino-2,3-dihydro-1H-inden-2-yl]-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide (Method 8, 350 mg, 0.73 mmol) was added to a solution of N-alpha-t-Boc-L-aspartic acid alpha-t-butyl ester (232 mg, 0.80 mmol), 1-hydroxybenzotriazole monohydrate (123 mg, 0.80 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (154 mg, 0.80 mmol), 4-methylmorpholine (0.18 mL, 1.6 mmol) in N,N-dimethylformamide (20 mL). The mixture was stirred at ambient temperature for 16 hours. The volatiles were removed by evaporation and the residue was dissolved in ethyl acetate (20 mL) and water (10 mL), the layers were separated before washing with 2M HCl then saturated NaHCO3. Evaporation afforded a white solid which was redissolved in dichloromethane (5 mL) and trifluoroacetic acid (5 mL), the solution was allowed to stir at ambient temperature for 2 hours. The volatiles were removed by evaporation and the residue triturated with ether, collected by filtration, washed with ether (2×10 ml) and dried to give the title compound (210 mg, 48%) as a white solid.

Provenance & Evidence