Piperidine → HCID 178456792, compound

HRID 624827Notes

Reaction equation

HRID 624827 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([F:37])=[C:13]([NH:15][C:16]2[CH:21]=[C:20]([NH:22][CH2:23][CH:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH3:25])[N:19]3[N:32]=[CH:33][C:34]([CH:35]=O)=[C:18]3[N:17]=2)[CH:14]=1.N1CCCCC1>C(O)C.O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([F:37])=[C:13]([NH:15][C:16]2[CH:21]=[C:20]([NH:22][CH2:23][CH:24]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH3:25])[N:19]3[N:32]=[CH:33][C:34]([CH:35]=[C:7]4[NH:1][C:2](=[O:3])[NH:4][C:5]4=[O:6])=[C:18]3[N:17]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 583140035-(5-Chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Product 1

HCID 178456792HCID 178456792, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Hydantoin (7 mg, 0.07 mmol) and 5-(5-chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (15 mg, 0.035 mmol) were dissolved in ethanol (0.5 mL) along with piperidine (7 uL, 0.07 mmol). The reaction was heated at 80° C. for 1 hour in the microwave. The reaction was then 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 5-((5-(5-chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (5 mg, 28% yield). LCMS (M+1=515)

Workup

  1. temperatureThe reaction was then 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-d9c84572c3cd4bc0b64aa3a065b5b32d
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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