Water → HCID 15481713, compound

HRID 1859008Notes

Reaction equation

HRID 1859008 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:24])([C@H:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[C:25](=O)([O-])[O-:26].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:24])([C@H:16]([N:18]1[CH2:19][CH2:20][N:21]([CH:25]=[O:26])[CH2:22][CH2:23]1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15481711HCID 15481711, compound

Product 1

HCID 15481713HCID 15481713, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of compound 2 (200 mg, 0.6 mmol) and potassium carbonate (248 mg, 1.8 mmol) in DMF (5 ml) was heated at 120° C. for 24 h. The contents were poured into cold water and extracted with ethyl acetate (3×20 ml). The combined organic extract was washed with water, brine and dried over sodium suphate. The solvent was removed under reduced pressure and the resulting product was purified on a column of silica gel (EtOAc/MeOH; 98:2) to give the title compound as colorless solid (80 mg, 36%).

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. extractionThe combined organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over sodium suphate
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting product was purified on a column of silica gel (EtOAc/MeOH; 98:2)

Sources & evidence

ORD record
ord-5291995885cd4f3790879776c5edf9b7
Source dataset
uspto-grants-2000_11
Patent number
US06153616

Reaction notes

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