Hydrochloric Acid → 1-[(2-chloropyridin-4-yl)methyl]-3-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethylimidazolidine-2,4-dione

HRID 546560Notes

Reaction equation

C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:13]3[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[CH:23]=4)[C:14]3=[O:29])[CH:11]=2)[C:6]([CH3:31])([CH3:30])[CH2:5]1)(=O)C.Cl>O1CCOCC1>[Cl:28][C:24]1[CH:23]=[C:22]([CH2:21][N:15]2[C:16]([CH3:20])([CH3:19])[C:17](=[O:18])[N:13]([C:10]3[CH:11]=[C:12]4[C:7]([C:6]([CH3:31])([CH3:30])[CH2:5][NH:4]4)=[CH:8][CH:9]=3)[C:14]2=[O:29])[CH:27]=[CH:26][N:25]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2.65 g of 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione obtained in stage h) below in 30 mL of dioxane are added 33 mL of aqueous 1N hydrochloric acid solution. The reaction mixture is heated at 70° C. for 17 hours and concentrated under reduced pressure. The residue is diluted with 30 mL of water and poured into saturated aqueous sodium hydrogen carbonate solution, and the precipitate formed is filtered off, washed with four times 10 mL of water and dried to give 2.3 g of 1-[(2-chloropyridin-4-yl)methyl]-3-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethylimidazolidine-2,4-dione in the form of a beige-coloured solid, the characteristics of which are as follows:

Workup

concentrationconcentrated under reduced pressure
additionThe residue is diluted with 30 mL of water
additionpoured into saturated aqueous sodium hydrogen carbonate solution
customthe precipitate formed
filtrationis filtered off
washwashed with four times 10 mL of water
customdried

Sources & evidence

ORD record: ord-8f54bd9382b84c9ca67a069010042b9a
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935819B2

Reaction notes

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