HCID 15428582, compound → HCID 9863977, compound

HRID 1421689Notes

Reaction equation

HRID 1421689 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.C([N:35]1[CH:39]=[C:38]([CH2:40][C:41]2[CH:48]=[CH:47][C:44]([C:45]#[N:46])=[CH:43][CH:42]=2)[N:37]=[CH:36]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CC#N>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:37]2[C:38]([CH2:40][C:41]3[CH:48]=[CH:47][C:44]([C:45]#[N:46])=[CH:43][CH:42]=3)=[CH:39][N:35]=[CH:36]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 15428582HCID 15428582, compoundHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

Product 1

HCID 9863977HCID 9863977, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(-2-Oxo-2-H-pyridin-1-yl)benzyl bromide from Step 3 (1.7 mmol, 450 mg ) and 4-(1-trityl-1H-imidazol-4-ylmethyl)benzonitrile (1.7 mmol) were suspended in CH3CN and heated to reflux for 3 hours. The reaction mixture was concentrated and the residue taken up in MeOH and refluxed for 2 hours. The MeOH was removed in-vacuo. The resulting oil was partitioned between EtOAc and saturated NaHCO3. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield an oil which was purified by flash chromatography using 5% IPA/CHCl3 saturated with NH3 as an eluent. Pure fractions were collected and concentrated to give a white solid. The solids were washed with warm 50% EtOAc/Hexane and collected on a frit. The white solid was collected and dried under high vacuum at 50° for 12 hours to give the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. temperaturerefluxed for 2 hours
  5. customThe MeOH was removed in-vacuo
  6. customThe resulting oil was partitioned between EtOAc and saturated NaHCO3
  7. extractionThe aqueous layer was extracted twice with EtOAc
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto yield an oil which
  13. customwas purified by flash chromatography
  14. customPure fractions were collected
  15. concentrationconcentrated
  16. customto give a white solid
  17. washThe solids were washed
  18. temperaturewith warm 50% EtOAc/Hexane
  19. customcollected on a frit
  20. customThe white solid was collected
  21. customdried under high vacuum at 50° for 12 hours

Sources & evidence

ORD record
ord-75b361bd740e456fae4a76d8af057ef4
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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