Pyridine → methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 3-necked 2-L flask fitted with a mechanical stirrer and a nitrogen inlet were charged the aminoindazole carbamate (94.5 g, 1.0 equiv.), N,N′-disuccinimidyl carbonate (113.8 g, 1.07 eq), and dry acetonitrile (950 mL, KF=0.06%). Pyridine (32.8 g, 1.0 eq) was added to the mixture and it was heated to 40° C. and stirred for 15 h during which time a solid precipitated. The solid was filtered, washed with fresh dry acetonitrile (3×100 mL), and dried in a vacuum oven at 40° C. to afford 130.1 g (92.9% potency adjusted) of the activated succinimidyl carbamate as a light brown solid.

Provenance & Evidence