Toluene → HCID 68584758, compound

HRID 17311Notes

Reaction equation

HRID 17311 reaction equation
[C:1]([C:3]1[C:4]([N-:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[C:5]([OH:18])[C:6]([F:17])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[C:8]=1[CH3:9])#[N:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[F:17][C:6]1[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)=[C:8]([CH3:9])[C:3]([C:1]#[N:2])=[C:4]2[C:5]=1[O:18][C:20]([CH:21]([CH3:23])[CH3:22])=[N:19]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 178428581HCID 178428581, compound

Product 1

HCID 68584758HCID 68584758, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(5-cyano-2-fluoro-3,3′-dihydroxy-6-methylbiphenyl-4-yl)isobutylamide (I-56) (60 mg, 0.183 mmol), p-toluenesulfonic acid monohydrate (10.4 mg, 0.0548 mmol) and toluene (5 ml) was heated under reflux for 2.5 hours. After cooling, this was diluted with ethyl acetate, successively washed with 1 N hydrochloric acid and saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (30.9 mg, 54%) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. washsuccessively washed with 1 N hydrochloric acid and saturated brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customto obtain a pale brown residue
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0cd8d4294833411bb7c929901a7c1dd2
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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