Water → HCID 178499321, compound

HRID 2211289Notes

Reaction equation

HRID 2211289 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:10]([O:12][CH3:13])=[O:11])=[C:5]2[C:9]=1[NH:8][CH:7]=[N:6]2.[H-].[Na+].C([N:35]1[C:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:46]2[CH:53]=[CH:52][C:49]([CH2:50]Br)=[CH:48][CH:47]=2)=[N:38][N:37]=[N:36]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>CN(C=O)C.C(Cl)(Cl)Cl.CO>[CH3:1][C:2]1[S:3][C:4]([C:10]([O:12][CH3:13])=[O:11])=[C:5]2[C:9]=1[N:8]=[CH:7][N:6]2[CH2:50][C:49]1[CH:52]=[CH:53][C:46]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[C:39]2[NH:35][N:36]=[N:37][N:38]=2)=[CH:47][CH:48]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178499323HCID 178499323, compound

Product 1

HCID 178499321HCID 178499321, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-methylthieno[3,4-d]-imidazole-6-carboxylate (0.20 g) in DMF (2 ml) was added sodium hydride (60% oil, 48 mg) under ice-cooling. The mixture was stirred for 15 minutes, and there which was added 4-[2'-(N-trityltetrazol-5-yl)phenyl]benzylbromide (0.68 g), followed by stirring for one hour at room temperature. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The concentrate was purified by silica gel column chromatography to give the first fraction and the second fraction. The oily substance obtained from the first fraction was dissolved in chloroform (3 ml) - methanol (12 ml), to which was added 1N-HC1 (0.5 ml), and the mixture was stirred for one hour at room temperature. The solvent was evaporated in vacuo. To the residue was added water, whose pH was adjusted to 3-4 with 1N NaOH, followed by extraction with chloroform. The extract was washed with water, dried and concentrated to dryness. The concentrate was purified by silica gel column chromatography. The crystals thus obtained were recrystallized from ethyl acetate -hexane to afford colorless needles (0.12 g, 28%), m.p. 188°-189° C.

Workup

  1. temperaturecooling
  2. stirringby stirring for one hour at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe concentrate was purified by silica gel column chromatography
  8. customto give the first fraction
  9. customThe oily substance obtained from the first fraction
  10. additionto which was added 1N-HC1 (0.5 ml)
  11. stirringthe mixture was stirred for one hour at room temperature
  12. customThe solvent was evaporated in vacuo
  13. additionTo the residue was added water, whose pH
  14. extractionfollowed by extraction with chloroform
  15. washThe extract was washed with water
  16. customdried
  17. concentrationconcentrated to dryness
  18. customThe concentrate was purified by silica gel column chromatography
  19. customThe crystals thus obtained
  20. customwere recrystallized from ethyl acetate -hexane

Sources & evidence

ORD record
ord-68f9ed8ac92e45f0ba20cbe39450c249
Source dataset
uspto-grants-1995_10
Patent number
US05463073

Reaction notes

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