Pyridine → HCID 54406910, compound

HRID 864676Notes

Reaction equation

HRID 864676 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:22])[CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[N:8]1[CH:12]=[C:11]([C:13]([OH:15])=O)[N:10]=[CH:9]1)[CH3:4].C(Cl)(=O)C(Cl)=O.N[C:30]1[C:42]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1.[N:43]1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[CH2:3]([O:5][C:6](=[O:22])[CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[N:8]1[CH:12]=[C:11]([C:13]([NH:43][CH:41]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:34]3[C:42]2=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:15])[N:10]=[CH:9]1)[CH3:4]

Participants

8

Reactant 5

HCID 1049PyridineHCID 22817Fluoren-1-amineHCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 54522466HCID 54522466, compound

Product 1

HCID 54406910HCID 54406910, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 0.062 g of 55% sodium hydride in oil in tetrahydrofuran was added to 0.4 g of 4-carboxy-α-hexyl-1H-imidazole-1-acetic acid ethyl ester. After 10 minutes of stirring, 0.125 ml of oxalyl chloride were added. After stirring for 2 hours at room temperature, 0.31 g of 1-aminofluorene were added followed by 0.16 ml of pyridine. The mixture was stirred at room temperature for 3 hours, taken up in ethyl acetate, and washed twice with a saturated citric acid solution followed by a water wash. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography using 1:1 ethyl acetate/hexane and silica gel was performed on the residue and the resulting fractions combined and concentrated in vacuo to provide the desired titled intermediate.

Workup

  1. stirringAfter stirring for 2 hours at room temperature
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. washwashed twice with a saturated citric acid solution
  4. washwash
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2381d29d8dc45abbcee3eb6d367d049
Source dataset
uspto-grants-1996_10
Patent number
US05563278

Reaction notes

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