Triethylamine → HCID 53477390, compound

HRID 1802538Notes

Reaction equation

HRID 1802538 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 44,054.398%

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-b0d90e849b7e44f6959f390e445de22f
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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