Methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)-5,6-dihydropyridin-1(2H)-yl)pyrazine-2-carboxylate → Methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)piperidin-1-yl)pyrazine-2-carboxylate

HRID 1479955Notes

Reaction equation

HRID 1479955 reaction equation
[CH2:1]([C:8]1[N:13]=[N:12][C:11]([C:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:21]=[CH:22][C:23]([C:26]([O:28][CH3:29])=[O:27])=[N:24][CH:25]=3)[CH2:16][CH:15]=2)=[C:10]([CH3:30])[C:9]=1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH2:1]([C:8]1[N:13]=[N:12][C:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:21]=[CH:22][C:23]([C:26]([O:28][CH3:29])=[O:27])=[N:24][CH:25]=3)[CH2:16][CH2:15]2)=[C:10]([CH3:30])[C:9]=1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59191506Methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)-5,6-dihydropyridin-1(2H)-yl)pyrazine-2-carboxylate

Product 1

HCID 67177357Methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)piperidin-1-yl)pyrazine-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 5-(4-(6-benzyl-4,5-dimethylpyridazin-3-yl)-5,6-dihydropyridin-1(2H)-yl)pyrazine-2-carboxylate (60 mg, 0.144 mmol) in 20 mL EtOH is added 10% Pd—C (77 mg, 72 mmol). The reaction mixture is stirred under hydrogen atmosphere for 16 h. The mixture is filtered through Celite and the filtrate is concentrated to afford a yellow solid (60 mg, 100%).

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-81b42a4b5b2a4963a86d89f02e0f7c2b
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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