Trifluoroacetic acid → HCID 136933045, compound

HRID 1477674Notes

Reaction equation

HRID 1477674 reaction equation
COC1C=CC(C[N:8]2[C:13]([CH3:14])=[N:12][C:11](SC)=[N:10][C:9]2=[O:17])=CC=1.FC(F)(F)C(O)=O.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C@@H:35]([OH:40])[CH2:36][NH:37][CH2:38][CH:39]=2)=[CH:30][CH:29]=1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.O.O1CCOCC1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C@@H:35]([OH:40])[CH2:36][N:37]([C:11]3[N:12]=[C:13]([CH3:14])[NH:8][C:9](=[O:17])[N:10]=3)[CH2:38][CH:39]=2)=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 117839254HCID 117839254, compoundHCID 117839615HCID 117839615, compound

Product 1

HCID 136933045HCID 136933045, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To 1-(4-methoxybenzyl)-6-methyl-4-(methylthio)-1,3,5-triazin-2(1H)-one (1.39 g, 5.0 mmol) synthesized in Reference Synthesis Example 315, trifluoroacetic acid (10 mL) was added and the resultant mixture was stirred for 1 hour under reflux. After completion of the reaction, the reaction solution was concentrated under reduced pressure and 1,4-dioxane (10 mL), (R)-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridin-3-ol (966 mg, 5.00 mmol) synthesized in Reference Synthesis Example 133, and N,N-diisopropylethylamine (1.92 g, 10.0 mmol) were added to the concentrated solution, followed by refluxing the resultant mixture for 2 hours. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1) to obtain the title compound (1.41 g, yield 94%).

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. additionwere added to the concentrated solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-3e4bfc40dd2840d2a0f3dda37410cb75
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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