HCID 118045370, compound → HCID 118046152, compound

HRID 595904Notes

Reaction equation

HRID 595904 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:10]=[CH:11][C:12]([CH:15]([C:23]#[N:24])[CH2:16][CH2:17][C:18](OCC)=[O:19])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Ni].C(O)C>[O:19]=[C:18]1[NH:24][CH2:23][CH:15]([C:12]2[N:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 118045370HCID 118045370, compound

Product 1

HCID 118046152HCID 118046152, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst3×HCID 702EthanolSolvent2×

Conditions

Temperature
56 °C

Procedure

Under Argon, to ethyl 4-(5-(tert-butoxycarbonylamino)pyrazin-2-yl)-4-cyanobutanoate in ethanol solution (94 mg, 0.281 mmol/8 mL) was added Raney Nickel catalyst ethanol suspension (Nickel in ˜2 mL ethanol, the amount of Raney Nickel was not accurately measured), and the reaction mixture was stirred under H2 balloon after 3 times air atomasphere exchange heated with external oil bath at 56° C. for overnight with H2 balloon. The reaction mixture was cooled down to room temperature, and filtered through a pad of Celite, the filtrate was concentrated to afford tert-butyl 5-(6-oxopiperidin-3-yl)pyrazin-2-ylcarbamate in a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered through a pad of Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a30025bddcd146cb9b2d13060a2e96e5
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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