Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 135703014, compound

HRID 398049Notes

Reaction equation

HRID 398049 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14](=O)[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[C:9]([O:11]CC)=O)=[CH:4][CH:3]=1.[C:22]1([CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH2:34])=[NH:33])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC1C=CC(C)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:11])[NH:34][C:32]([CH2:31][CH2:30][CH2:29][CH2:28][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:33][C:14]=2[C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18767876HCID 18767876, compoundHCID 18767926HCID 18767926, compound

Product 1

HCID 135703014HCID 135703014, compound

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

Ethyl 2-(4-fluorophenyl)-3-oxo-3-(4-pyridyl)-propionate (293 mg, 1.02 mmol), 4-phenylbutanecarboxamidine (315 mg, 1.79 mmol) and pyridinium p-toluenesulfonate (10 mg) were suspended in p-xylene (10 ml). With efficient stirring, the mixture was heated to reflux using a Dean-Stark apparatus with continuous removal of water. After 16 h, the solvent was evaporated and the product purified by column chromatography on silica gel (3% methanol/dichloromethane) followed by recrystallization from acetone. MS (m/z): 400.3 (M+H)+; C25H22FN3O requir. 399.5.

Workup

  1. temperatureWith efficient stirring, the mixture was heated
  2. temperatureto reflux
  3. customwith continuous removal of water
  4. customthe solvent was evaporated
  5. customthe product purified by column chromatography on silica gel (3% methanol/dichloromethane)
  6. customfollowed by recrystallization from acetone

Sources & evidence

ORD record
ord-54d0170d2085445092657dfd9e8a8757
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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