Benzyl 4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)piperidine-1-carboxylate → 1-(piperidin-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

HRID 2204496Notes

Reaction equation

HRID 2204496 reaction equation
[C:1]1([CH:13]2[CH2:18][CH2:17][N:16](C(OCC3C=CC=CC=3)=O)[CH2:15][CH2:14]2)[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[N:3][N:2]=1>CO.[Pd]>[NH:16]1[CH2:15][CH2:14][CH:13]([C:1]2[N:5]3[C:6]4[CH:12]=[CH:11][NH:10][C:7]=4[N:8]=[CH:9][C:4]3=[N:3][N:2]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 136198878Benzyl 4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)piperidine-1-carboxylate

Product 1

HCID 1361988561-(piperidin-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazineYield 82.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)piperidine-1-carboxylate (0.34 g, 0.90 mmol, Example #2, Step A) and 10% Pd on carbon (0.10 g, 0.09 mmol) in MeOH (30 mL) was shaken under hydrogen at about 60 psi for about 5 h at ambient temperature. The reaction was filtered through Celite® and concentrated under reduced pressure to constant weight to afford 1-(piperidin-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine as a yellow solid (0.18 g, 77%): LC/MS (Table 2, Method a) Rt=0.70 min; MS m/z: 243 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. concentrationconcentrated under reduced pressure to constant weight

Sources & evidence

ORD record
ord-beafaaec42174e88a66c13236cdb446c
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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