Piperidine → HCID 178503290, compound

HRID 624810Notes

Reaction equation

HRID 624810 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=O)=[C:9]3[N:8]=[C:7]([S:16][CH3:17])[CH:6]=2)[CH2:3][CH2:2]1.[NH:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[O:20].N1CCCCC1>C(O)C>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:24]4/[C:22](=[O:23])[NH:21][C:19](=[O:20])[NH:18]/4)=[C:9]3[N:8]=[C:7]([S:16][CH3:17])[CH:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58313837HCID 58313837, compound

Product 1

HCID 178503290HCID 178503290, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The above product 7-(cyclopropylamino)-5-(methylthio)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde was dissolved in 20.0 mL ethanol, added hydantoin (2.82 g, 28.17 mmol) and piperidine (2.70 mL). The reaction was heated to 80° C. for overnight. Cooled the reaction mixture and yellow precipitate was filtered, washed with ethanol, dried to yield (Z)-5-((7-(cyclopropylamino)-5-(methylthio) pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione 4.18 g (90% yield). LCMS (M+1=331)

Workup

  1. temperatureCooled the reaction mixture and yellow precipitate
  2. filtrationwas filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-3cae76c119d348c3ba38dd1fa026247d
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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