Cesium carbonate → HCID 117925825, compound

HRID 1477722Notes

Reaction equation

HRID 1477722 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][N:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=4)[C:16](=[O:28])[N:15]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:41][C:42]([F:45])([F:44])[F:43])(=O)=O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][N:17]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([O:27][CH2:41][C:42]([F:45])([F:44])[F:43])=[CH:25][CH:26]=4)[C:16](=[O:28])[N:15]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 117839212HCID 117839212, compound

Product 1

HCID 117925825HCID 117925825, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide solution of 4-[4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-(4-hydroxybenzyl)-1,3,5-triazin-2(1H)-one (10.0 mg, 0.0260 mmol) synthesized in Synthesis Example 483a, cesium carbonate (10.3 mg, 0.0320 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (4.57 μL, 0.0320 mmol) were added and the resultant mixture was stirred at 70° C. for 2 and a half hours. After the completion of the reaction, the reaction solution was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1/1) to obtain the title compound (2.43 mg, yield: 14%).

Workup

  1. additionwere added
  2. customAfter the completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe resultant residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c2c995c51e2d402b9d61c9ddf7709440
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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