Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68585126, compound

HRID 17507Notes

Reaction equation

HRID 17507 reaction equation
[C:1]1([C:6]([O:8][C:9]2[C:10]([F:25])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([CH3:18])=[C:13]([C:16]#[N:17])[C:14]=2[NH2:15])=O)[CH2:5][CH2:4][CH2:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([C:6]2[O:8][C:9]3[C:14](=[C:13]([C:16]#[N:17])[C:12]([CH3:18])=[C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:10]=3[F:25])[N:15]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 866308604-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate

Product 1

HCID 68585126HCID 68585126, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate (I-213) (180 mg, 0.54 mmol) was dissolved in xylene (50 ml), pyridinium p-toluenesulfonate (50 mg) was added, followed by heating under reflux for 5 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The resulting residue was diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (4:1, v/v) to obtain the entitled compound (148 mg, 87%) as a white crystal.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customthe solvent was evaporated away under reduced pressure
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. washeluted with a mixed solvent of n-hexane/ethyl acetate (4:1

Sources & evidence

ORD record
ord-cd068948037a46c1a9ace3ee6761f9ff
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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