Imidazole → HCID 23144757, compound

HRID 337433Notes

Reaction equation

HRID 337433 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([NH:11][C:12]2[S:13][C:14]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:15]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[O:10])[CH:6]=[CH:5][N:4]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.O>CN(C=O)C>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:15]1[N:16]=[C:12]([NH:11][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)[CH:8]=2)=[O:10])[S:13][C:14]=1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 23144585HCID 23144585, compound

Product 1

HCID 23144757HCID 23144757, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Compound 107 (150 mg, 0.387 mmol) was dissolved in DMF (2 ml), and imidazole (129 mg, 1.89 mmol) was added thereto, followed by stirring at 90° C. for 3 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=30:1) to afford the entitled Compound 108 (120 mg, 74%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-cc4cdbd2235c4143805ff4a90ce06d8c
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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