HCID 58010221, compound → HCID 58010231, compound

HRID 2204609Notes

Reaction equation

HRID 2204609 reaction equation
[CH:1]1[C:9]2[N:8]3[C:10]([CH:13]4[CH:18]([CH3:19])[CH2:17][CH2:16][N:15](C(OCC5C=CC=CC=5)=O)[CH2:14]4)=[CH:11][N:12]=[C:7]3[CH:6]=[N:5][C:4]=2[NH:3][CH:2]=1.[H][H]>[Pd].CCO>[CH3:19][CH:18]1[CH2:17][CH2:16][NH:15][CH2:14][CH:13]1[C:10]1[N:8]2[C:9]3[CH:1]=[CH:2][NH:3][C:4]=3[N:5]=[CH:6][C:7]2=[N:12][CH:11]=1

Participants

5

Reactant 2

HCID 58010221HCID 58010221, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58010231HCID 58010231, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylpiperidine-1-carboxylate (0.55 g, 1.4 mmol) and palladium on carbon (10%, 0.38 g, 0.36 mmol) in EtOH (25 mL) was hydrogenated at room temperature under an atmospheric pressure of hydrogen for about 20 h. The catalyst was removed by filtration through a Celite® pad and the filtrate was concentrated in vacuo to give 8-(4-methylpiperidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.30 g, 83%) as a yellow amorphous solid: LC/MS (Table 2, Method a) Rt=0.93 min; MS m/z: 256 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through a Celite® pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-08c205b69e774075a4b0ae3a131a32ad
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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