Cesium carbonate → HCID 66802601, compound

HRID 341420Notes

Reaction equation

HRID 341420 reaction equation
[C:1]1([NH:7][C:8]2[N:13]=[C:12]([NH2:14])[N:11]=[C:10]([C:15]3[N:19]=[C:18]([C:20]4[CH:21]=[N:22][C:23]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:24][CH:25]=4)[O:17][N:16]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][CH2:40][O:41][CH3:42]>CN(C=O)C>[CH3:42][O:41][CH2:40][CH2:39][N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[N:13]=[C:12]([NH2:14])[N:11]=[C:10]([C:15]2[N:19]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH2:27][C:28]([F:30])([F:29])[F:31])=[CH:24][CH:25]=3)[O:17][N:16]=2)[N:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 56943046HCID 56943046, compound

Product 1

HCID 66802601HCID 66802601, compoundYield 2.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-N-Phenyl-6-{5-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine (prepared in an analogous manner to Example 41, 0.100 g, 0.232 mmol) was added to cesium carbonate (0.151 g, 0.465 mmol) in DMF (3 mL) at room temperature followed by the addition of 1-bromo-2-methoxyethane (22 μL, 0.232 mmol). The reaction mixture was stirred at room temperature for 1 h and then heated to 50 C for 18 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain a brown solid. The solid was purified by preparative HPLC, Method A to afford the title compound (2.8 mg, 2.5%).

Workup

  1. temperatureheated to 50 C for 18 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a brown solid
  10. customThe solid was purified by preparative HPLC, Method A

Sources & evidence

ORD record
ord-21e889bb24cb4c599faf81845dbf280a
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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