Hydrazine → HCID 86627657, compound

Participants

Reaction Conditions

Reaction Steps

Anhydrous hydrazine (0.481 mL, 15.3 mmol) was added, to a stirred suspension of N-[4-(8-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butyl]benzamide (prepared as described in Part B of Example 89, 2.86 g, 5.11 mmol) in ethanol (50 mL). The reaction was stirred overnight and then was concentrated under reduced pressure. Methanol (25 mL) was added and the mixture was cooled to 0° C. Acetaldehyde (2.9 mL) was added and the reaction mixture was stirred overnight. The reaction mixture was concentrated partially under reduced pressure, then 1 M aqueous sodium hydroxide (50 mL) was added and the mixture was sonicated for 1 minute. The solid was isolated by filtration, washed with water, and dried under vacuum at 70° C. to provide a 3:1 ratio of oxime isomers of N-{4-[8-({[ethylideneamino]oxy}methyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}benzamide.

Provenance & Evidence