Ammonia → HCID 58447012, compound

HRID 1045759Notes

Reaction equation

HRID 1045759 reaction equation
[C:1]([C:3]1[C:4]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:5][CH:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)#[N:2].N>CO.[Ni]>[NH2:2][CH2:1][C:3]1[C:4]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:5][CH:6]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58446992HCID 58446992, compound

Product 1

HCID 58447012HCID 58447012, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A 100 mL round bottom flask was charged with tert-butyl 4-(3-cyano-5-(thiophen-2-yl)pyrazin-2-yl)piperazine-1-carboxylate (0.75 g, 2.01 mmol), Raney Ni (200 mg) and 2 M solution of NH3 in MeOH (50 mL). The resulting mixture was stirred at room temperature overnight under H2 atmosphere. Work-up: the reaction mixture was filtered. The filtrated was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with 5% MeOH in CH2Cl2, to afford 680 mg (89%) of the product.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrated was concentrated in vacuo
  3. customthe residue was purified by flash column chromatography on silica gel with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-63361fe7b05043159b1cba08e0fa3342
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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