Imidazole → HCID 23144615, compound

HRID 1967748Notes

Reaction equation

HRID 1967748 reaction equation
Br[CH2:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[O:8])=[CH:5][CH:4]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.O>CN(C=O)C>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:13]1[N:14]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:26]=[CH:27][C:3]([CH2:2][N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[CH:4][CH:5]=2)[S:11][C:12]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 23144355HCID 23144355, compound

Product 1

HCID 23144615HCID 23144615, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Compound 59 (448 mg, 1.00 mmol) was dissolved in DMF (4 mL), imidazole (204 mg, 3.00 mmol) was added thereto, followed by stirring at 65° C. for 2 hours. Water was added to the reaction mixture, 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=20:1) to afford the entitled Compound 60 (348 mg, 80%).

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=20:1)

Sources & evidence

ORD record
ord-e4cfed64c1ca4a30a3833afc3ded301c
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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