Piperidine → HCID 178503330, compound

HRID 2037035Notes

Reaction equation

HRID 2037035 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:8]1([NH:11][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:21]=O)=[C:16]3[N:15]=[C:14]([S:23][CH3:24])[C:13]=2[C:25]#[N:26])[CH2:10][CH2:9]1.N1CCCCC1>C(O)C.O>[CH:8]1([NH:11][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:21]=[C:7]4[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]4)=[C:16]3[N:15]=[C:14]([S:23][CH3:24])[C:13]=2[C:25]#[N:26])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 86654659HCID 86654659, compound

Product 1

HCID 178503330HCID 178503330, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Hydantoin (366 mg, 3.7 mmol) and 7-(cyclopropylamino)-3-formyl-5-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile (1 g, 3.7 mmol) were dissolved in ethanol (18.5 mL) along with piperidine (3.7 mL, 3.7 mmol). The reaction was heated at 80° C. After 10 hours, the reaction was cooled to r.t., diluted with water, and the precipitate was collected and washed with water, 1:1 ethanol:water, then ethanol. The yellow solid was dried in vacuo to give the intermediate, 7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)-5-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile (1.1 g, 83% yield). LCMS (M+1=356)

Workup

  1. temperaturethe reaction was cooled to r.t.
  2. customthe precipitate was collected
  3. washwashed with water, 1:1 ethanol
  4. customThe yellow solid was dried in vacuo

Sources & evidence

ORD record
ord-03f12fd5ce9a4248837228de917ae3db
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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