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

HRID 1857752Notes

Reaction equation

HRID 1857752 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[C:17](=[O:22])[NH:18][CH:19]=[CH:20][CH:21]=3)[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].C(N(CC)CC)C.O>O1CCCC1.CO>[C:30]([O:24][CH2:23][C:13]1[N:14]([CH2:15][C:16]2[C:17](=[O:22])[NH:18][CH:19]=[CH:20][CH:21]=2)[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:25]([CH3:27])[CH3:26])[N:12]=1)(=[O:31])[NH2:32]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76400Trichloroacetyl isocyanateHCID 22130742HCID 22130742, 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 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 20 ml of tetrahydrofuran was dissolved 200 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(2-oxo-1,2-dihydro-pyridin-3-yl)methyl-4-isopropyl-1H-imidazole (116b), and 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-b21b9caf75ba4834abbbfdc861663f63
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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