Potassium Hydroxide → HCID 10288045, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 0.30 g (0.54 mmol) of (7R,8R,9R)-10-acetyl-3-bromo-8-(2-methoxyethoxy)-2-methyl-9-phenyl-7-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, 0.10 ml (0.60 mmol) aqueous potassium hydroxide (6 N) and 0.20 ml (5.14 mmol) hydrazine hydrate in methanol is stirred al 60° C. for 4 h. The methanol is removed in vacuo and the reaction mixture is diluted with water. Subsequently the mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (toluene/dioxane/acetic acid: 8/1/1) to give 0.12 g (0.28 mmol/52%) of the title compound as an amorphous solid. 1H-NMR (200 MHz, [D6] DMSO): δ=2.30 (s, 1H), 3.09 (s, 1H), 3.10-3.30 (m, 2H), 3.45-3.70 (m, 2H), 4.48 (d, 1H), 4.68 (d, 1H), 6.96 (d, 1H), 7.20-7.51 (m, 5H), 7.58 (d, 1H).

Provenance & Evidence