p-Toluenesulfonic acid monohydrate → HCID 117839213, compound

HRID 1477719Notes

Reaction equation

HRID 1477719 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][C:16]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)(O)[CH:15]([OH:27])[CH2:14]3)=[N:9][C:8]2=[O:28])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][CH:16]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[C:15](=[O:27])[CH2:14]3)=[N:9][C:8]2=[O:28])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117925778HCID 117925778, compound

Product 1

HCID 117839213HCID 117839213, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution (10 mL) of 1-(4-chlorobenzyl)-4-[4-(4-fluorophenyl)-3,4-dihydroxypiperidin-1-yl]-1,3,5-triazin-2(1H)-one (202 mg, 0.468 mmol) synthesized in Synthesis Example 91 and p-toluenesulfonic acid monohydrate (341 mg, 1.99 mmol) was stirred under reflux by heating for 4 hours. After the completion of the reaction, the reaction solution was concentrated under reduced pressure and to the resultant residue, saturated sodium bicarbonate aqueous solution was added, and extraction with ethyl acetate was performed. The organic layer was concentrated under reduced pressure and the resultant residue was purified by reverse-phase column chromatography (water/acetonitrile) to obtain the title compound (15.0 mg, yield: 8%).

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 4 hours
  3. customAfter the completion of the reaction
  4. concentrationthe reaction solution was concentrated under reduced pressure and to the resultant residue, saturated sodium bicarbonate aqueous solution
  5. additionwas added
  6. extractionextraction with ethyl acetate
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customthe resultant residue was purified by reverse-phase column chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-7831f9555aac445d9ef4e4508f730de9
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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