Methanol → HCID 25230564, compound

HRID 1961720Notes

Reaction equation

HRID 1961720 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:22]=[N:23]O)=[N:11][CH:12]=[C:13]([N:15]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[N:16]3)[N:14]=2)=[CH:4][CH:3]=1.CO>[Ni].C(O)C>[NH2:23][CH2:22][C:10]1[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:14][C:13]([N:15]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[N:16]2)=[CH:12][N:11]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 136331521HCID 136331521, compound

Product 1

HCID 25230564HCID 25230564, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (50% slurry in water, 1 mL) was added to a solution of 3-(4-chloro-phenylamino)-5-(3,5-dimethyl-pyrazol-1-yl)-pyrazine-2-carbaldehyde oxime (60 mg, 0.17 mmol) in ethanol (99%, 6 mL). The reaction mixture was stirred under a hydrogen atmosphere for one hour. Methanol was added followed by filtration and evaporation. The crude product was purified by flash chromatography (dichloromethane/methanol as eluent) to give [3-aminomethyl-6-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-(4-chloro-phenyl)-amine (16 mg, 28%) as a white solid. Mp.=156-160° C.

Workup

  1. filtrationfollowed by filtration and evaporation
  2. customThe crude product was purified by flash chromatography (dichloromethane/methanol as eluent)

Sources & evidence

ORD record
ord-6856d31154d04bbaad129067ec11a9ac
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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