Water → 2(1H)-Pyridinone, 3-((2-(((aminocarbonyl)oxy)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1H-imidazol-1-yl)methyl)-

HRID 1416062Notes

Reaction equation

HRID 1416062 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15]N3C=CC=CC3=O)[C:13]([CH2:23][OH:24])=[N:12][C:11]=2[CH:25]([CH3:27])[CH3:26])[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:30]([N:32]=C=O)=[O:31].[CH2:37]([N:39](CC)CC)C.O.[O:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1>CO>[C:30]([O:24][CH2:23][C:13]1[N:14]([CH2:15][C:48]2[C:49](=[O:45])[NH:39][CH:37]=[CH:46][CH:47]=2)[C:10]([S:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([CH:25]([CH3:26])[CH3:27])[N:12]=1)(=[O:31])[NH2:32]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 474060HCID 474060, compound

Product 1

HCID 4740612(1H)-Pyridinone, 3-((2-(((aminocarbonyl)oxy)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1H-imidazol-1-yl)methyl)-Yield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-40 °C

Procedure

In 20 ml of tetrahydrofuran was dissolved 200 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(1,2-dihydro-2-oxopyridinylmethyl)-4-isopropyl-1H-imidazole (116b), the mixture was cooled to -40° C. Under stirring, 84 μl of trichloroacetylisocyanate was added, the mixture was allowed to stand to reach room temperature, and stirred for 30 minutes. There were added 500 μl of triethylamine, 5 ml of water and 5 ml of methanol, and the mixture was stirred at 70° C. for 1 hour. After completion of the reaction, the solution was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crystals were washed with diethyl ether, filtered, and 177 mg of Compound I-132 was obtained (yield 80%)mp 214° C.

Workup

  1. customto reach room temperature
  2. stirringstirred for 30 minutes
  3. stirringthe mixture was stirred at 70° C. for 1 hour
  4. customAfter completion of the reaction
  5. distillationthe solution was distilled off under reduced pressure
  6. additionan aqueous sodium hydrogen carbonate solution was added
  7. extractionextracted with ethyl acetate
  8. dry with materialthe extract was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. washThe crystals were washed with diethyl ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-0f2b27d83249482a8951272a6eede3b7
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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