Hydrochloric Acid → HCID 178435049, compound

HRID 1290231Notes

Reaction equation

HRID 1290231 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]([C:9]1[N:10]=[CH:11][N:12](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=1)O.Cl.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>CCO.[OH-].[OH-].[Pd+2]>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:9]1[N:10]=[CH:11][NH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 444972Fumaric AcidHCID 10526927HCID 10526927, compound

Product 1

HCID 178435049HCID 178435049, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of (2-methylthien-3-yl)-1-trityl-imidazol-4-yl-methanol (1.5 g, 3.5 mmol) was combined with HCl (3.4 mmol) and Pd(OH)2 (1.5 g) in EtOH and hydrogenated (55 psi) at 55° C. for 48 hrs. The catalyst was removed by filtration through Dicalite and the solvent was evaporated in vacuo. The residue was dissolved in water, washed twice with Et2 O, and then basified with Na2CO3 and extracted twice with EtOAc. The combined extracts were dried (K2CO3), filtered and solvent evaporated. The residue was chromatographed on flash silica gel (99:0.75:0.25 EtOAc/MeOH/NH4OH) to give a thick syrup which was dissolved in 2-PrOH and combined with fumaric acid (116 mg). The solvent was evaporated and the residue recrystallized from acetone to give the target compound, m.p. 140°-141° C. 1H NMR (DMSO-d6) supported the assigned structure: δ6 2.3 (s, 3H), 3.75 (s, 2H), 6.6 (s, 2H), 6.75 (s, 1H), 6.85 (d, J=5.3 Hz, 1H), 7.15 (d, 1H), 7.65 (s, 1H). Elemental Analysis: Calc. for C9H10N2 S.C4H4O4C, 53.05; H, 4.79; N, 9.52. Found C, 53.22; H, 4.87; N, 9.50.

Workup

  1. customThe catalyst was removed by filtration through Dicalite
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washwashed twice with Et2 O
  5. extractionextracted twice with EtOAc
  6. dry with materialThe combined extracts were dried (K2CO3)
  7. filtrationfiltered
  8. customsolvent evaporated
  9. customThe residue was chromatographed on flash silica gel (99:0.75:0.25 EtOAc/MeOH/NH4OH)
  10. customto give a thick syrup which
  11. customThe solvent was evaporated
  12. customthe residue recrystallized from acetone
  13. customto give the target compound, m.p. 140°-141° C

Sources & evidence

ORD record
ord-e19fb67c824e45d7bd8de273606bb1e9
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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