Piperidine → HCID 178483884, compound

HRID 383684Notes

Reaction equation

HRID 383684 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([CH:22]=O)=[C:15]3[N:14]=2)=[CH:8][CH:7]=1.[NH:25]1[CH2:31][C:29](=[O:30])[NH:28][C:26]1=[O:27].N1CCCCC1>CCO>[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([CH:22]=[C:31]4[NH:25][C:26](=[O:27])[NH:28][C:29]4=[O:30])=[C:15]3[N:14]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 58196835HCID 58196835, compound

Product 1

HCID 178483884HCID 178483884, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To 5-(4-(2-(dimethylamino)ethoxy)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (90 mg, 0.276 mmol) in EtOH was added hydantoin (28 mg, 0.276 mmol) and piperidine (28 μL, 0.276 mmol). The mixture was heated at 70° C. overnight three times. Solvent was removed under reduced pressure and MeOH was added. Insolubilities were filtered off, and the filtrate was purified by HPLC to yield 5-((5-(4-(2-(dimethylamino)ethoxy)phenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=408)

Workup

  1. customSolvent was removed under reduced pressure and MeOH
  2. additionwas added
  3. filtrationInsolubilities were filtered off
  4. customthe filtrate was purified by HPLC

Sources & evidence

ORD record
ord-efeaef09b8854d8c8105be8831364abb
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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