Water → HCID 178487442, compound

HRID 346979Notes

Reaction equation

HRID 346979 reaction equation
[Li]CCCC.[CH3:6][N:7]1[CH:11]=[N:10][NH:9][C:8]1=[S:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([O:32][CH3:33])[CH:26]=[C:25]3[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)=[O:21])=[CH:16][CH:15]=1.O>C1COCC1>[Cl:40][C:36]1[CH:35]=[C:34]([C:25]2[C:24]3[C:29](=[CH:30][CH:31]=[C:22]([C:20]([C:17]4[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=4)([C:11]4[N:7]([CH3:6])[C:8]([SH:12])=[N:9][N:10]=4)[OH:21])[CH:23]=3)[N:28]=[C:27]([O:32][CH3:33])[CH:26]=2)[CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12561623H-1,2,4-Triazole-3-thione, 2,4-dihydro-4-methyl-HCID 21578663(4-Chlorophenyl)[4-(3-chlorophenyl)-2-methoxy-6-quinolinyl]methanoneHCID 178418339Butyllithium

Product 1

HCID 178487442HCID 178487442, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

BuLi (0.233 mol) was added dropwise at −70° C. to a solution of 2,4-dihydro-4-methyl-3H-1,2,4-triazole-3-thione (0.0612 mol) in THF (350 ml) under N2 flow. The mixture was stirred at −70° C. for 1 hour and then brought to 0° C. The mixture was stirred at 0° C. for 45 minutes and then cooled to −70° C. A solution of intermediate (56) (0.0612 mol) in THF (150 ml) was added. The mixture was then brought to 0° C., poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: Cyclohexane/EtOAc 70/30; 15–35 μm). The pure fractions were collected and the solvent was evaporated, yielding 11.06 g (35%) of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(5-mercapto-4-methyl-4H-1,2,4triazol-3-yl)-2-methoxy-6-quinolinemethanol (intermediate 57), mp. >260° C.

Workup

  1. custombrought to 0° C
  2. stirringThe mixture was stirred at 0° C. for 45 minutes
  3. temperaturecooled to −70° C
  4. customwas then brought to 0° C.
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography over silica gel (eluent: Cyclohexane/EtOAc 70/30; 15–35 μm)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6b9c60f1b36e49c39bed9d057fff7bc7
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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