Piperidine → HCID 178518487, compound

HRID 624693Notes

Reaction equation

HRID 624693 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:18][CH2:17]3)[N:12]3[N:19]=[CH:20][C:21]([CH:22]=O)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH:24]1[CH2:30][C:28](=[O:29])[NH:27][C:25]1=[O:26].N1CCCCC1>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:17][CH2:18]3)[N:12]3[N:19]=[CH:20][C:21]([CH:22]=[C:30]4[NH:24][C:25](=[O:26])[NH:27][C:28]4=[O:29])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10006HydantoinHCID 53240562HCID 53240562, compound

Product 1

HCID 178518487HCID 178518487, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To 5-(3-chlorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (26 mg, 0.08 mmol) in EtOH was added hydantoin (8 mg, 0.08 mmol) and piperidine (8 μl, 0.08 mmol). The mixture was stirred at 70° C. over the weekend. Insolubilities were filtered off, and filtrate was concentrated under reduced pressure. Filtrate was then dissolved in MeOH and isolated by prep HPLC to yield 5-((5-(3-chlorophenylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=410)

Workup

  1. filtrationInsolubilities were filtered off
  2. concentrationfiltrate was concentrated under reduced pressure
  3. dissolutionFiltrate was then dissolved in MeOH
  4. customisolated by prep HPLC

Sources & evidence

ORD record
ord-e940f166a48443bdb7bf187a970f49fb
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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