Hydrochloric Acid → 1-[(2-Aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride

HRID 546581Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26]C(=O)C)[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:31]>O1CCOCC1>[ClH:31].[NH2:26][C:22]1[CH:21]=[C:20]([CH2:19][N:13]2[C:14]([CH3:18])([CH3:17])[C:15](=[O:16])[N:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=3)[C:12]2=[O:30])[CH:25]=[CH:24][N:23]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 1.8 g of N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)acetamide obtained in stage b) below in 40 mL of dioxane are added 20.8 mL of 1N hydrochloric acid solution. The mixture is heated at 75° C. for six hours, 42 mL of 1N hydrochloric acid solution are then added and stirring is continued for 36 hours at the same temperature. The solution is then concentrated under reduced pressure to give 1.4 g of 1-[(2-aminopyridin-4-yl)methyl]-3-(4-tert-butylphenyl)-5,5-dimethylimidazolidine-2,4-dione hydrochloride in the form of a white powder, the characteristics of which are as follows:

Workup

concentrationThe solution is then concentrated under reduced pressure

Sources & evidence

ORD record: ord-642ca73b440b4d9c97997e894ff8f8c5
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935819B2

Reaction notes

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