HCID 20035429, compound → HCID 131715990, compound

HRID 1905408Notes

Reaction equation

HRID 1905408 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=O)=[CH:4][CH:3]=1.[NH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([CH3:32])[O:31][CH2:30][CH2:29][O:28]2)=[CH:23][CH:22]=1>C(O)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:18][O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3([CH3:32])[O:28][CH2:29][CH2:30][O:31]3)=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 20035429HCID 20035429, compoundHCID 20035447HCID 20035447, compound

Product 1

HCID 131715990HCID 131715990, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.1 Gram (0.0043 mole) of 5-(4-fluorophenoxy)-1,3-dimethylpyrazol-4-carbaldehyde and 0.9 g (0.0043 mole) of 2-[4-(aminooxymethyl)phenyl]-2-methyl-1,3-dioxolane were added to 20 ml of ethanol, and the resulting mixture was heated for 3 hours to carry out reaction. After completion of the reaction, ethanol was removed by evaporation under reduced pressure, after which water was added to the residue and extraction was carried out with ethyl acetate. The ethyl acetate extract was washed with water and dried, and ethyl acetate was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silca gel to obtain 1.3 g of the desired compound.

Workup

  1. temperaturethe resulting mixture was heated for 3 hours
  2. customreaction
  3. customwas removed by evaporation under reduced pressure
  4. additionafter which water was added to the residue and extraction
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customethyl acetate was removed by evaporation
  9. customto obtain an oily product
  10. customThis oily product was column-chromatographed on silca gel

Sources & evidence

ORD record
ord-491e2810dd4f48d4a76db44371e39567
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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