1-(4-{3-[1-(1H-Benzoimidazole-2-carbonyl)-azetidin-3-YL]-pyrazin-2-YL}-3,6-dihydro-2H-pyridin-1-YL)-ethanone → 1-(4-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-1-yl)-ethanone

HRID 1850333Notes

Reaction equation

HRID 1850333 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:17]([C:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:30])[CH3:29])[CH2:26][CH:27]=3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:13]1)=[O:11]>CO.[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([C:16]2[C:17]([CH:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:30])[CH3:29])[CH2:26][CH2:27]3)=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:13]1)=[O:11]

Participants

4

Reactant 1

HCID 585468551-(4-{3-[1-(1H-Benzoimidazole-2-carbonyl)-azetidin-3-YL]-pyrazin-2-YL}-3,6-dihydro-2H-pyridin-1-YL)-ethanone

Product 1

HCID 585468241-(4-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-1-yl)-ethanoneYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(4-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-3,6-dihydro-2H-pyridin-1-yl)-ethanone (170 mg, 0.42 mmol) and wet Pd—C (50%, 50 mg) in MeOH (30 mL) was stirred under H2 (30 psi) at RT for 2 h then the reaction mixture was filtered through CELITE® and washed with MeOH. The filtrate was concentrated in vacuo and the residue was purified by ISCO silica gel column (10% to 50% EtOAc in petroleum ether) to give 1-(4-{3-[1-(1H-benzoimidazole-2-carbonyl)-azetidin-3-yl]-pyrazin-2-yl}-piperidin-1-yl)-ethanone (101 mg, 0.25 mmol, 60% yield).

Workup

  1. filtrationthe reaction mixture was filtered through CELITE®
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by ISCO silica gel column (10% to 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-2e91afb5e4b24ce2aa47b0fdfb2da7ec
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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