HCID 71076731, compound → HCID 86676099, compound

HRID 1774507Notes

Reaction equation

HRID 1774507 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[CH:10]=[C:9]([S:11]CC2C=CC(OC)=CC=2)[CH:8]=[N:7]1)[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[CH:10]=[C:9]([S:11][S:11][C:9]2[CH:8]=[N:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH:10]=2)[CH:8]=[N:7]1)[CH3:2]

Participants

3

Reactant 1

HCID 71076731HCID 71076731, compound

Product 1

HCID 86676099HCID 86676099, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

[4-(4-Methoxy-benzylsulfanyl)-pyrazol-1-yl]-acetic acid ethyl ester (1.96 g, 6.4 mmol) was dissolved in trifluoroacetic acid (20 mL) and heated to 70° C. overnight. The temperature was increased to 120° C. and the reaction stirred overnight again. The reaction mixture was concentrated, azeotroping with toluene, then purified via silica gel chromatography (0-100% EtOAc in hexanes) to yield the title compound.

Workup

  1. temperatureThe temperature was increased to 120° C.
  2. concentrationThe reaction mixture was concentrated
  3. customazeotroping with toluene
  4. custompurified via silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a6a70a86feae409e96330b73547a876f
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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