HCID 178522887, compound → HCID 178522888, compound

HRID 2289981Notes

Reaction equation

HRID 2289981 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[CH:15][C:14]=3[C:25]([F:28])([F:27])[F:26])=[O:9])=[CH:4][CH:3]=1>C(OCC)C.CCCCCC.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:15][C:14]=3[C:25]([F:28])([F:26])[F:27])=[O:9])=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 178522887HCID 178522887, compound

Product 1

HCID 178522888HCID 178522888, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584099Diethylether hexaneSolvent

Procedure

N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-8-(trifluoromethyl)-3-quinolinecarboxamide (397 mg) from Example No. 121 is dissolved in methanol/dichloromethane (1/1, 87 mL) and palladium on carbon (5%, 80 mg) are added. The mixture is placed under a hydrogen atmosphere (28 psi) for 1 h, filtered through celite, and concentrated. The crude product is purified by column chromatography (dichloromethane/methanol, 100/1 to 100/3) to afford 43 mg (10%) of the title compound as a white solid.

Workup

  1. customfor 1 h
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe crude product is purified by column chromatography (dichloromethane/methanol, 100/1 to 100/3)

Sources & evidence

ORD record
ord-be38ec63769f48569d163da4766bf854
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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