Methanol → HCID 178438813, compound

HRID 2290002Notes

Reaction equation

HRID 2290002 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][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]O)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.CO.C#C>C(Cl)Cl.[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][CH3:23])=[CH:15][CH:14]=3)=[O:9])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178522861HCID 178522861, compound

Product 1

HCID 178438813HCID 178438813, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Example No. 134 (500 mg) and Pd/C (10%, 100 mg) is dissolved in 80 mL 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 30 psi and monitored by mass spectroscopy for complete reduction of the acetylene. The old palladium catalyst is replaced with fresh palladium catalyst each time the reaction is taken off the Parr. The reaction mixture is filtered over celite to remove the palladium. The filtrate is condensed. The crude solid is adsorbed onto silica and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 16.3 mg (3%) of the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture is filtered over celite
  2. customto remove the palladium
  3. customcondensed
  4. customchromatographed
  5. washeluting with 2% MeOH in CH2Cl2
  6. customcondensed

Sources & evidence

ORD record
ord-eded96fedddd4ec7ac1489f854852ce6
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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