Piperidine → HCID 178518471, compound

HRID 383696Notes

Reaction equation

HRID 383696 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][N:18]4[N:21]=[CH:22][C:23]([CH:24]=O)=[C:17]4[N:16]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:2]1.[NH:26]1[CH2:32][C:30](=[O:31])[NH:29][C:27]1=[O:28].N1CCCCC1.CO.C(Cl)Cl>CCO>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][N:18]4[N:21]=[CH:22][C:23]([CH:24]=[C:32]5[NH:26][C:27](=[O:28])[NH:29][C:30]5=[O:31])=[C:17]4[N:16]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 10006HydantoinHCID 21226129Dichloromethane methanolHCID 58196499HCID 58196499, compound

Product 1

HCID 178518471HCID 178518471, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To 5-(3-(morpholinomethyl)phenylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (56 mg, 0.166 mmol) in EtOH was added hydantoin (16.6 mg, 0.166 mmol) and piperidine (16.8 μL, 0.166 mmol). The mixture was heated at 70° C. overnight. The solid formed was filtered off and filtrated prepared by HPLC then TLC (1% MeOH/DCM) to yield 5-((5-(3-(morpholinomethyl)phenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=420)

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. filtrationfiltrated
  4. customprepared by HPLC

Sources & evidence

ORD record
ord-e0e648db324342b799e78d61bf2232c5
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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