HCID 22054788, compound → HCID 178509714, compound

HRID 1829865Notes

Reaction equation

HRID 1829865 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]=[CH:27][CH:26]=[C:25]([C:29]#N)[CH:24]=1)=[NH:22]>CO>[C:21]([C:23]1[CH:24]=[C:25]([C:29]2[NH:10][CH2:9][C:8]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:11]=2)[CH:26]=[CH:27][CH:28]=1)#[N:22]

Participants

4

Reactant 2

HCID 22054788HCID 22054788, compoundHCID 552656943-Cyano-benzimidic acid methyl ester

Product 1

HCID 178509714HCID 178509714, compoundYield 51.1%

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 3-cyanobenzeneimidic acid methyl ester (792 mg), and the mixture was stirred at room temperature for 18 hrs. After concentrating the reaction mixture, the residue was dissolved in ethyl acetate (30 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=3:1→2:1) to give the objective compound (370 mg).

Workup

  1. concentrationAfter concentrating the reaction mixture
  2. dissolutionthe residue was dissolved in ethyl acetate (30 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=3:1→2:1)

Sources & evidence

ORD record
ord-3619e680be4a45209a8ceb75c2e8b95f
Source dataset
uspto-grants-2006_06
Patent number
US07064142B2

Reaction notes

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