Ethyl Acetate → HCID 59548857, compound

HRID 1810969Notes

Reaction equation

HRID 1810969 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:24]([O-])=O)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][N:16]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(OCC)(=O)C>[Pt]=S.CO>[NH2:24][C:4]1[C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:23])[CH2:15][N:16]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17]3)[CH2:12][CH2:13]2)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59548836HCID 59548836, compound

Product 1

HCID 59548857HCID 59548857, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 82861Platinum sulfide (PtS)CatalystHCID 887MethanolSolvent

Procedure

A round bottom flask is charged with 5% platinum sulfide on carbon (0.200 g, 0.039 mmol). The flask is evacuated and refilled with argon three times. To the flask is added 1-[4-(5-chloro-3-nitro-pyridin-2-yl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone (1.10 g, 2.90 mmol) as a solution in a 1:1 mixture of ethyl acetate:methanol (100 mL). The mixture is placed under an atmosphere of hydrogen and stirred for 5 h at room temperature. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to provide 0.67 g of 1-[4-(3-amino-5-chloro-pyridin-2-yl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone as a white solid in 66% yield.

Workup

  1. customThe flask is evacuated
  2. additionrefilled with argon three times
  3. filtrationThe mixture is filtered through a pad of diatomaceous earth
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41afde44df6c4c0f8f36074a883bcc13
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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