Imidazole → HCID 19592683, compound

HRID 613538Notes

Reaction equation

HRID 613538 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[CH2:14][OH:15])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])([OH:3])=[O:2].N1C=CN=C1.[Si:32](Cl)([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O>[Si:32]([O:15][CH2:14][C:13]1[C:12]2[C:7](=[C:8]([NH:16][C:17](=[O:26])[C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[C:1]([OH:3])=[O:2])([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 19592713HCID 19592713, compound

Product 1

HCID 19592683HCID 19592683, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-carboxy-8-(2,6-dichlorobenzoylamino)-4-hydroxymethylquinoline (1.11 g) in dimethylformamide were added imidazole (637 mg) and tert-butyldiphenylsilyl chloride (2.57 g) under ice-cooling, and the mixture was stirred for 5 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. To the solution of the obtained residue in dioxane (10 ml) was added 1N sodium hydroxide solution (2.9 ml), and the mixture was stirred for 30 minutes at ambient temperature. The mixture was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in isopropyl alcohol-diisopropyl ether, and insoluble material was filtered off. The filtrate was concentrated in vacuo to give 4-(tert-butyldiphenylsilyloxymethyl)-3-carboxy-8-(2,6-dichlorobenzoylamino)quinoline (1.22 g).

Workup

  1. temperaturecooling
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionTo the solution of the obtained residue in dioxane (10 ml) was added 1N sodium hydroxide solution (2.9 ml)
  7. stirringthe mixture was stirred for 30 minutes at ambient temperature
  8. additionThe mixture was diluted with water
  9. washwashed with diethyl ether
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water and brine
  12. dry with materialdried over magnesium sulfate
  13. customevaporated in vacuo
  14. dissolutionThe residue was dissolved in isopropyl alcohol-diisopropyl ether
  15. filtrationinsoluble material was filtered off
  16. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-444d2fefdeb145e7bb723f81816cc694
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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