Ethyl Acetate → HCID 90933494, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with tert-butyl-3-ethyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate (2.45 g, 4.55 mmol) and 1,4-dioxane (24 mL) to give a brown solution. TEA (2.54 mL, 18.2 mmol) was added followed by the addition of SOCl2 (0.50 mL, 6.8 mmol). The reaction mixture was heated at about 80° C. for about 5 h. The mixture was cooled to ambient temperature and EtOAc (100 mL) and water (30 mL) were added. The layers were partitioned and the organic layer was washed with water (2×30 mL) and brine (2×30 mL), dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give a brown residue. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH/DCM. The product-containing fractions were combined and concentrated to give tert-butyl (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate (1.7 g, 71%): LC/MS (Table 2, Method a) Rt=2.50 min; MS m/z: 525 (M+H)+.

Provenance & Evidence