Toluene → HCID 178438607, compound

HRID 2062644Notes

Reaction equation

HRID 2062644 reaction equation
CS[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:21][CH:20]=3)=[C:14]([CH2:33][CH2:34][CH3:35])[N:13]3[N:36]=[CH:37][N:38]=[C:12]23)[CH2:7][CH2:6]1.S(Cl)(Cl)(=O)=[O:40].[C:44]1([CH3:50])[CH:49]=[CH:48][CH:47]=CC=1>>[OH:40][C:44]1([CH2:3][O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]5[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:21][CH:20]=4)=[C:14]([CH2:33][CH2:34][CH3:35])[N:13]4[N:36]=[CH:37][N:38]=[C:12]34)[CH2:7][CH2:6]2)[CH2:49][CH2:48][CH2:47][CH2:50]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24648Sulfuryl chlorideHCID 178438689HCID 178438689, compound

Product 1

HCID 178438607HCID 178438607, compoundYield 2.4%

Procedure

4′-[(4-{trans-4-[(Methylsulfanyl)methoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (1.0 g) was dissolved in toluene (10 mL), and sulfuryl chloride (0.16 mL) was added at 0° C. The mixture was stirred at room temperature for 2 hr, the precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was mixed with cyclopentanone (0.16 g) and tetrahydrofuran (10 mL), and samarium iodide (57 mL, 0.1 M tetrahydrofuran solution) was added dropwise at room temperature under an argon atmosphere. The mixture was stirred at room temperature for 65 hr and added to saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.026 g, 2.4%).

Workup

  1. filtrationthe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was mixed with cyclopentanone (0.16 g) and tetrahydrofuran (10 mL), and samarium iodide (57 mL, 0.1 M tetrahydrofuran solution)
  4. additionwas added dropwise at room temperature under an argon atmosphere
  5. stirringThe mixture was stirred at room temperature for 65 hr
  6. additionadded to saturated aqueous ammonium chloride solution
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfece3b0aede47e2a86836af579ee86a
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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