Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68584553, compound

HRID 17562Notes

Reaction equation

HRID 17562 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([F:17])[C:3]=1[O:18][C:19]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH:21]1([C:19]2[O:18][C:3]3[C:2](=[C:7]([C:8]#[N:9])[C:6]([CH3:10])=[C:5]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:4]=3[F:17])[N:1]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86630879HCID 86630879, compound

Product 1

HCID 68584553HCID 68584553, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

(4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl)cyclopentanecarboxylate (I-274) (200 mg, 0.83 mmol) was dissolved in xylene (50 ml), then pyridinium p-toluenesulfonate (50 mg) was added, followed by heating under reflux for 18 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified by preparative TLC (ethyl acetate:n-hexane=1:2, v/v) to obtain the entitled compound (112 mg, 59%) as a colorless amorphous substance.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 18 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 magnesium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customThe resulting residue was purified by preparative TLC (ethyl acetate

Sources & evidence

ORD record
ord-5c887d611f3a483db6c0651dfdb86efb
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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