Piperidine → HCID 178518489, compound

HRID 624694Notes

Reaction equation

HRID 624694 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].N1CCCCC1.[CH:14]1([NH:17][C:18]2[N:23]3[N:24]=[CH:25][C:26]([CH:27]=O)=[C:22]3[N:21]=[C:20]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)[CH:19]=2)[CH2:16][CH2:15]1>C(O)C.O>[CH:14]1([NH:17][C:18]2[N:23]3[N:24]=[CH:25][C:26](/[CH:27]=[C:7]4/[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]/4)=[C:22]3[N:21]=[C:20]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)[CH:19]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58313818HCID 58313818, compound

Product 1

HCID 178518489HCID 178518489, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Hydantoin (69 mg, 0.69 mmol) and piperidine (69 μL, 0.69 mmol) were added to 7-(cyclopropylamino)-5-(3-fluorophenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (72 mg, 0.23 mmol) dissolved in ethanol (1.1 mL). The reaction was heated at 80° C. After 15 h, the reaction was cooled to r.t., diluted with water (5 mL), and the precipitate was collected and washed with 1:1 ethanol:water (5 mL). The bright yellow solid was dried in vacuo to give (Z)-5-((7-(cyclopropylamino)-5-(3-fluorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (25 mg, 10% over 3 steps). LCMS (M+1=507)

Workup

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

Sources & evidence

ORD record
ord-c060a17a37f14396b075813e6303b0f5
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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