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Piperidine → HCID 178501994, compound

HRID 624701
Notes
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Reaction equation

HRID 624701 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]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH:6]=2)[CH2:3][CH2:2]1.[NH:21]1[CH2:27][C:25](=[O:26])[NH:24][C:22]1=[O:23].N1CCCCC1>C(O)C>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:27]4\[NH:21][C:22](=[O:23])[NH:24][C:25]\4=[O:26])=[C:9]3[N:8]=[C:7]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH:6]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58313737Methyl 7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylcarbamate

Product 1

HCID 178501994HCID 178501994, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To methyl 7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylcarbamate (33 mg, 0.12 mmol) in 1.0 mL ethanol was added hydantoin (12 mg, 0.12 mmol) and piperidine (11 ul). The reaction was heated at 80° C. for two hours. The reaction was cooled to room temperature, the yellow precipitate was filtered, and washed with ethanol to yield 15 mg (40% yield) (Z)-methyl 7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-ylcarbamate. LCMS (M+1=358)

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe yellow precipitate was filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-9c26e8e5b3e34a2f838e9ef53cf7c878
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09303033B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes