Hydrochloric Acid → HCID 57626032, compound

Participants

Reaction Steps

To a solution of 400 mg of tert-butyl [2-(6-{3-[(2-chloropyridin-4-yl)methyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]isopropylcarbamate obtained in stage a) below in 15 mL of dioxane are successively added, under argon, 88 mg of N,N-dimethylurea, 39 mg of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (Xantphos), 30 mg of palladium acetate and 872 mg of caesium carbonate. The reaction mixture is refluxed for 4 hours and filtered, and the filtrate is concentrated under reduced pressure. The residue is taken up in 30 mL of ethyl acetate, washed with three times 15 mL of water, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (90/10 by volume) to give 280 mg of a yellow lacquer, which is taken up in 10 mL of a 4N solution of hydrogen chloride in dioxane and stirred for 17 hours at room temperature. The reaction mixture is then concentrated under reduced pressure and is triturated in 20 mL of ethyl ether and the solid formed is filtered off and dried to give 200 mg of 3-[4-({3-[1-(N-isopropylglycyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}methyl)pyridin-2-yl]-1,1-dimethylurea in hydrochloride form, the characteristics of which are as follows:

Provenance & Evidence