Water → HCID 474049, compound

HRID 1416061Notes

Reaction equation

HRID 1416061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:17]=[N:18][C:19](=[O:22])[CH2:20][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[CH:17]=[N:18][C:19](=[O:22])[CH2:20][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 4740592(1H)-Pyridinone, 5-((5-((3,5-dichlorophenyl)thio)-2-(hydroxymethyl)-4-(1-methylethyl)-1H-imidazol-1-yl)methyl)-

Product 1

HCID 474049HCID 474049, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 10 ml of tetrahydrofuran was dissolved 51 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(5,6-dihydro-6-oxopyridin-3-ylmethyl)-4-isopropyl-1H-imidazole (116a), and the mixture was cooled to -40° C. Under stirring, 22 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, 1 ml of water and 2 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 residue was purified by silica gel chromatography (ethyl acetate:methanol=10:1)to give 46 mg of Compound I-131 was obtained (yield 82%).

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. customThe residue was purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-6a0db7533a3249c0abfc6ea28d4d7f94
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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