p-Toluenesulfonic acid → HCID 66720869, compound

HRID 1639926Notes

Reaction equation

HRID 1639926 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[N:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=2[NH:26][N:27]=[C:28]([C:35]2C=CC=CC=2)[C:29]2C=CC=[CH:31][CH:30]=2)[CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:41]C(=O)CC(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]2[N:21]=[C:20]([C:22]([O:24][CH2:25][CH3:41])=[O:23])[CH:19]=[CH:18][C:17]=2[N:26]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:35])=[N:27]2)[CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31261AcetylacetoneHCID 86637364HCID 86637364, compound

Product 1

HCID 66720869HCID 66720869, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

Put 600 mg (1.08 mmol) of methyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-[2-(diphenylmethylidene)hydrazino]pyridine-2-carboxylate, 378 mg (3.78 mmol) of 2,4-pentanedione, 186 mg (1.08 mmol) of paratoluenesulphonic acid and 5 mL of ethanol in a screw-top bottle. Heat the mixture at 120° C. while stirring for 48 h, then cool, and concentrate under reduced pressure. Then distribute the residue in 50 mL of EtOAc and 50 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a heptane/EtOAc gradient from 0 to 50% of EtOAc. After concentration under reduced pressure, we obtain 235 mg of ethyl 6-[3-(benzyloxy)-4-chlorophenyl]-5-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine-2-carboxylate in the form of oil.

Workup

  1. temperaturecool
  2. concentrationconcentrate under reduced pressure
  3. dry with materialDry the organic phase over Na2SO4
  4. concentrationconcentrate under reduced pressure
  5. customPurify the residue
  6. customobtained by silica gel column chromatography
  7. washeluting with a heptane/EtOAc gradient from 0 to 50% of EtOAc
  8. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-068d1a451fb646839b2382c54eb6354e
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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