Triethylamine → HCID 53477390, compound

HRID 888296Notes

Reaction equation

HRID 888296 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[OH:18][C:19]1([C:25]#[C:26][C:27]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:27]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)=[CH:26][C:25]([C:19]3([OH:18])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77023(4-Methoxyphenyl)hydrazineHCID 58399458HCID 58399458, compound

Product 1

HCID 53477390HCID 53477390, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 4-methoxyphenylhydrazine (165 mg, 0.944 mmol) in ethanol (5.0 mL), triethylamine (258 μL, 1.88 mmol) was added, and the obtained solution was stirred at room temperature for 30 minutes. The resulting solution was added to a solution of 3-(1-hydroxycyclohexyl)-1-(4-tolyl)-2-propyn-1-one (Reference Example 14) (214 mg, 0.883 mmol) in ethanol (3.0 mL), and the resulting mixture was stirred at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure, and distilled water was added to the residue. The resulting solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the title compound (141 mg, 0.389 mmol, 44%) as a yellow amorphous product.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for 20 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. distillationdistilled water
  5. additionwas added to the residue
  6. extractionThe resulting solution was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2823e327f0c9422781da1afb89c9c797
Source dataset
uspto-grants-2012_08
Patent number
US08247569B2

Reaction notes

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