2-Bromoethanol → HCID 56940968, compound

HRID 341414Notes

Reaction equation

HRID 341414 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:14]=[C:13]([NH2:24])[N:12]=2)[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][OH:34]>CN(C=O)C>[NH2:24][C:13]1[N:12]=[C:11]([C:8]2[N:7]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:10][N:9]=2)[N:16]=[C:15]([N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:32][CH2:33][OH:34])[N:14]=1

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 11430Potassium Carbonate2×HCID 56942720HCID 56942720, compound

Product 1

HCID 56940968HCID 56940968, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(5-Furan-2-yl-[1,2,4]oxadiazol-3-yl)-N-phenyl-[1,3,5]triazine-2,4-diamine (prepared in an analogous manner to Example 2, 100 mg, 310 μmol) and potassium carbonate (86 mg, 620 μmol) were stirred together in a sealed tube in DMF (5 ml). 2-Bromoethanol (26 μL, 310 μmol) was added and the reaction was heated at 110 C for 18 h. Potassium carbonate (43 mg, 310 μmol) and 2-bromoethanol (26 μL, 310 μmol) were added and the reaction stirred at 110 C for a further 18 h. After cooling and evaporation of the solvent the crude residue was dissolved in water (30 mL) and extracted twice with DCM (30 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude residue was purified using prep HPLC method B to give the desired title compound (14 mg, 12%).

Workup

  1. temperaturethe reaction was heated at 110 C for 18 h
  2. temperatureAfter cooling
  3. customevaporation of the solvent the crude residue
  4. dissolutionwas dissolved in water (30 mL)
  5. extractionextracted twice with DCM (30 mL)
  6. washThe combined organic extracts were washed with brine (30 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude residue was purified

Sources & evidence

ORD record
ord-900f704115c046cbb49d13c56fea640b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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