Acetic Acid → HCID 178517893, compound

HRID 1477566Notes

Reaction equation

HRID 1477566 reaction equation
C(O)(=O)C.Cl[C:6]1[NH:11][C:10](=[O:12])[N:9]=[C:8]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[N:7]=1>[OH-].[Pd+2].[OH-].O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:15][CH2:14][N:13]([C:8]3[N:7]=[CH:6][NH:11][C:10](=[O:12])[N:9]=3)[CH2:18][CH2:17]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1369330476-Chloro-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one

Product 1

HCID 178517893HCID 178517893, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

An acetic acid (15 mL)-water (35 mL) mixed solution of 6-chloro-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (1.00 g, 3.23 mmol) synthesized in Reference Synthesis Example 2 and palladium hydroxide-activated carbon catalyst (100 mg) was stirred under hydrogen atmosphere at room temperature for 3 days. After completion of the reaction, the reaction solution was filtered with Celite and the filtered residue was washed with methanol, followed by concentrating the obtained solution under reduced pressure. Toluene was added to the residue and the mixture was azeotropically dehydrated four times. The obtained residue was dried under reduced pressure to obtain the title compound (876 mg, yield 99%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered with Celite
  3. washthe filtered residue was washed with methanol
  4. concentrationby concentrating the obtained solution under reduced pressure
  5. additionToluene was added to the residue
  6. customThe obtained residue was dried under reduced pressure

Sources & evidence

ORD record
ord-0c38336ab92949b691340a14b220604c
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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