HCID 22267292, compound → HCID 22267286, compound

HRID 488874Notes

Reaction equation

HRID 488874 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:32])[CH2:10][C:11]2[C:12](=[O:31])[O:13][C:14]3[C:19]([C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][C:17]2[CH2:27][CH2:28][CH:29](O)[C:16]=2[CH:15]=3)=[C:4]([C:33]([F:36])([F:35])[F:34])[CH:3]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:32])[CH2:10][C:11]2[C:12](=[O:31])[O:13][C:14]3[C:19]([C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][C:17]2[CH2:27][CH:28]=[CH:29][C:16]=2[CH:15]=3)=[C:4]([C:33]([F:36])([F:34])[F:35])[CH:3]=1

Participants

3

Reactant 1

HCID 22267292HCID 22267292, compound

Product 1

HCID 22267286HCID 22267286, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-[4-fluoro-2-(trifluoromethyl)phenyl]-2-(8-hydroxy-2-oxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)acetamide (Example 214) (250 mg) in toluene (50 ml) was combined with p-TsOH monohydrate (300 mg), and heated under reflux for 30 minutes. After the reaction solution was concentrated, the resultant residue was purified by a silica gel column chromatography (eluent: hexane-ethyl acetate=3:1) to obtain the title compound as a colorless crystal (200 mg, yield: 74%). An aliquot was recrystallized from THF to measure a melting point. Melting point: 217-218° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. concentrationAfter the reaction solution was concentrated
  4. customthe resultant residue was purified by a silica gel column chromatography (eluent: hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-89bafcb899e14a139855d8e351efeaf4
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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