Methanol → HCID 178521993, compound

HRID 2290008Notes

Reaction equation

HRID 2290008 reaction equation
[C:1]1([NH:7][C:8](=[O:36])[O:9][CH2:10][C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([F:23])[CH:22]=2)[N:19]=[CH:18][C:17]([C:24]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[O:25])=[C:16]3[OH:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.C#C>C(Cl)Cl.[Pd]>[C:1]1([NH:7][C:8](=[O:36])[O:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([F:23])[CH:22]=2)[N:19]=[CH:18][C:17]([C:24]([NH:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:25])=[C:16]3[OH:35])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178521992HCID 178521992, compound

Product 1

HCID 178521993HCID 178521993, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-{[(4-chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-quinolinyl)-2-propynyl phenylcarbamate from Example No. 150 (100 mg) and Pd/C (10%, 20 mg) is dissolved in 80 mL 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 25 psi H2 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 is complete in 40 min . The reaction mixutre is filtered over celite to remove the palladium. The filtrate is condensed. The mixture is adsorbed onto silica and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 11.3 mg (11%) of the title compound as a white solid.

Workup

  1. filtrationThe reaction mixutre 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-6cce65dd7dca4987bd8d04553260b270
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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