Methyl pyrazine-2-carboximidate → HCID 178505491, compound

HRID 1455303Notes

Reaction equation

HRID 1455303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([NH2:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.CO[C:21]([C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1)=N>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[CH2:9][NH:10][C:21]([C:23]3[CH:28]=[N:27][CH:26]=[CH:25][N:24]=3)=[N:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 470894Methyl pyrazine-2-carboximidateHCID 22054788HCID 22054788, compound

Product 1

HCID 178505491HCID 178505491, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-bis(4-fluorophenyl)-1,2-ethanediamine (500 mg) in methanol (10 mL) was added pyrazineimidic acid methyl ester (385 mg), and the mixture was stirred at room temperature for 18 hrs. After concentrating the reaction mixture, the residue was dissolved in ethyl acetate (50 ml), washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution in this order, and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=1:1) to give the objective compound (446 mg).

Workup

  1. concentrationAfter concentrating the reaction mixture
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. customthe organic solvent was evaporated in vacuo
  7. customThe obtained residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-133a289879474a7b9bc073e70259f67e
Source dataset
uspto-grants-2009_01
Patent number
US07482358B2

Reaction notes

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