Imidazole → HCID 15347011, compound

HRID 1736134Notes

Reaction equation

HRID 1736134 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:14]2[C:15](=[O:29])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[C:21]([F:28])[CH:20]=3)[O:18][C:13]=2[C:12]([F:30])=[CH:11][C:10]=1[F:31].[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[F:31][C:10]1[CH:11]=[C:12]([F:30])[C:13]2[O:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[C:21]([F:28])[CH:20]=3)=[CH:16][C:15](=[O:29])[C:14]=2[C:9]=1[NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 15347008HCID 15347008, compound

Product 1

HCID 15347011HCID 15347011, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (1.01 mmol) of Compound 59 obtained in Example 59 was dissolved in 10 ml of tetrahydrofuran, 137 mg imidazole and 80 mg of sodium hydride (60% oil dispersion) were added and the mixture was heated at reflux for 2.3 hours. At 1.5 hours after the reaction was started, 40 mg of sodium hydride (60% oil disperison) was added. An aqueous solution of ammonium chloride was added to the reaction solution and the mixture was extracted with chloroform. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol:triethylamine=200:10:1) and triturated with n-hexane to give Compound 64 which was converted into hydrochloride according to the same manner as that in Example 16 to give 447 mg (73%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2.3 hours
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol:triethylamine=200:10:1)
  8. customtriturated with n-hexane

Sources & evidence

ORD record
ord-837cf70f151f470c8e8badf2193f2e79
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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