Dimethylformamide → 4-[4-(4-Fluorophenyl)piperazin-1-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one

HRID 1477692Notes

Reaction equation

HRID 1477692 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:24]=[CH:23][NH:22][C:21](=[O:25])[N:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.CC1C=CC(S(O[CH2:37][C:38]2[S:39][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:42]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[N:24]=[CH:23][N:22]([CH2:37][C:38]4[S:39][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:42]=4)[C:21](=[O:25])[N:20]=3)[CH2:17][CH2:18]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 117839221[5-(Trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate2×HCID 178517893HCID 178517893, compound

Product 1

HCID 1179254934-[4-(4-Fluorophenyl)piperazin-1-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-oneYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide solution (1 mL) of 4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (50.0 mg, 0.18 mmol) synthesized in Reference Synthesis Example 3, [5-(trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate (121 mg, 0.36 mmol) synthesized in Reference Synthesis Example 51 and potassium carbonate (99 mg, 0.72 mmol) were added and the resultant mixture was stirred at 80° C. for 2 hours. To the reaction solution, [5-(trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate (500 mg, 0.48 mmol) was added and the resultant reaction solution was stirred further for 2 hours. After the completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant reaction solution was performed three times. The organic layer was washed with brine, was dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (9.4 mg, yield: 12%).

Workup

  1. additionwere added
  2. customthe resultant reaction solution
  3. customreaction solution
  4. washThe organic layer was washed with brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-a5217f96a53b4da6993e62cf9f4aef6f
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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