Water → 2-((S)-5-methyl-2,4-dioxoimidazolidin-1-yl)-N-(1,2,3,4-tetrahydroacridin-9-yl)acetamide

HRID 1608776Notes

Reaction equation

C(O[C:4](=[O:26])[C@H:5]([CH3:25])[NH:6][CH2:7][C:8]([NH:10][C:11]1[C:12]2[C:17]([N:18]=[C:19]3[C:24]=1[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])C.[NH2:27][C:28](N)=[O:29].O>CN1CCCC1=O>[CH3:25][C@@H:5]1[N:6]([CH2:7][C:8]([NH:10][C:11]2[C:12]3[C:17]([N:18]=[C:19]4[C:24]=2[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[C:28](=[O:29])[NH:27][C:4]1=[O:26]

Participants

Conditions

Temperature: 80 °C

Procedure

In 9 ml of N-methylpyrrolidone, was dissolved 3.9 g of the compound obtained in Example 38, and 2.64 g of urea was further added thereto. The reaction was carried out at 160° C. for one hour. The reaction mixture was cooled to 80° C. and 100 ml of water was added. The precipitated crystals were collected by filtration and dissolved in a mixture of 5 ml of methanol and 150 ml of chloroform. The solution was dried over anhydrous sodium sulfate and evaporated to dryness. The obtained product was recrystallized from ethanol-ethyl acetate to obtain 2.44 g of the titled compound having the melting point of 260° to 263° C.

Workup

additionwas further added
filtrationThe precipitated crystals were collected by filtration
dissolutiondissolved in a mixture of 5 ml of methanol and 150 ml of chloroform
dry with materialThe solution was dried over anhydrous sodium sulfate
customevaporated to dryness
customThe obtained product was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record: ord-dd641394ad97459c843e8067c19e7108
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05397785

Reaction notes

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