Acetic Acid → HCID 135703328, compound

HRID 1657157Notes

Reaction equation

HRID 1657157 reaction equation
[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][CH:16]([N:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])[C:15]([C:24]3[CH:29]=[CH:28][C:27]([O:30]C(F)F)=[CH:26][CH:25]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1.C(O)(C)(C)C.CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1>[F:35][C:2]([F:1])([F:34])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][CH:16]([N:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])[C:15]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6386tert-ButanolHCID 18980963HCID 18980963, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 135703328HCID 135703328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 25.5 g (50.8 mmole) of N-(4-trifluoromethoxyphenyl)-3-(4-difluoromethoxyphenyl)-4-(N-methyl-N-(methoxycarbonyl)amino)-4,5-dihydro-1H-pyrazole-1-carboxamide dissolved in 25 g of tetrahydrofuran and 25 g of t-butanol was added 10 g of potassium t-butoxide. The mixture was refluxed for 1 hour and an additional 3.5 g of potassium t-butoxide was added. After refluxing an additional hour the mixture was acidified with acetic acid, concentrated in vacuo, and partitioned between methylene chloride and water. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and chromatographed over silica gel using hexane and diethyl ether to yield the expected compound, a white solid, mp 228°-233° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter refluxing an additional hour the mixture
  3. concentrationconcentrated in vacuo
  4. custompartitioned between methylene chloride and water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customchromatographed over silica gel

Sources & evidence

ORD record
ord-a4c8f54ebfdb42caa45865e7b52a9d7b
Source dataset
uspto-grants-1993_10
Patent number
US05256670

Reaction notes

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