HCID 136388387, compound → HCID 12151359, compound

HRID 393151Notes

Reaction equation

HRID 393151 reaction equation
O[N:2]=[CH:3][C:4]1[C:9]([CH:10]([N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]([CH3:13])[CH3:12])=[CH:8][N:7]=[CH:6][N:5]=1>C(Cl)(Cl)Cl>[C:3]([C:4]1[C:9]([CH:10]([N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]([CH3:12])[CH3:13])=[CH:8][N:7]=[CH:6][N:5]=1)#[N:2]

Participants

3

Reactant 1

HCID 136388387HCID 136388387, compound

Product 1

HCID 12151359HCID 12151359, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.25 g (0.77 mmol) of N-[1-(4-hydroxyiminomethylpyrimidin-5-yl)-2-methylpropyl]-N-methylphenylacetamide was dissolved in 30 ml of chloroform, and 0.16 g (0.83 mmol) of 1-(3-(dimethylamino)propyl]-3-ethylcarbodilmide hydrochloride was added and reacted at room temperature for 8 hours. After completion of the reaction, the solvent was distilled off, and water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and an aqueous sodium chloride solution in this order, dried and concentrated, and the obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.19 g (yield: 88%) of N-[1-(4-cyanopyrimidin-5-yl)-2-methylpropyl]-N-methylphenylacetamide as colorless crystals (melting point: 80-81° C.).

Workup

  1. customreacted at room temperature for 8 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionwater was added
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution in this order, dried
  8. concentrationconcentrated
  9. customthe obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-367072c4e02f40a884f2d1beb726a17b
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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