Acetic Anhydride → HCID 68089211, compound

Participants

Reaction Steps

Acetic anhydride (0.58 mL, 6.13 mmol), sodium formate (625 mg, 9.19 mmol) diisopropylethylamine (1.06 mL, 6.13 mmol) and anhydrous DMF (10 mL) were added to a 50 mL glass pressure tube. The cap was sealed and reaction allowed to stir for 30 min To this mixture was then added (R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carboxylic acid {1-[1-(4-iodo-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-amide (2.35 g, 3.07 mmol) as a solution in 5 mL of anhydrous DMF, followed by lithium chloride (389 mg, 9.19 mmol) and palladium acetate (34 mg, 0.15 mmol). The mixture was capped and then allowed to stir at 80° C. in an oil bath overnight (20 h). The reaction was cooled to room temperature. The reaction was diluted with 2N HCl (15 mL) and extracted with ethyl acetate (2×20 mL). The combined organics were dried (MgSO4) and concentrated. The residual material was dissolved in DMF and purified by reversed phase HPLC using 30-100% CH3CN/H2O as gradient to afford 1.56 g of the title compound.

Provenance & Evidence