HCID 16073857, compound → HCID 9823825, compound

HRID 1067263Notes

Reaction equation

HRID 1067263 reaction equation
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]#[C:16][CH2:17][OH:18])=[CH:12][CH:13]=2)[C:8](=[O:19])[C:7]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:21])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C1COCC1.CO.[Pt]=O>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:12][CH:13]=2)[C:8](=[O:19])[C:7]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:21])=[CH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 16073857HCID 16073857, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9823825HCID 9823825, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 303 mg of 1-(tert-butyl)-N-(4-chlorobenzyl)-6-(3-hydroxy-1-propynyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 11 and 15 mg of platinum oxide in 10 mL of 1: 1 THF-methanol is stirred under 1 atm of hydrogen gas for 3 h, then filtered through diatomaceous earth and concentrated under reduced pressure. The mixture was purified by flash chromatography on silica using 2-3% methanol in dichloromethane to afford 294 mg of the title compound.

Workup

  1. customfrom Preparation No
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated under reduced pressure
  4. customThe mixture was purified by flash chromatography on silica using 2-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-bd8949bcc5cf4520aa44f2fc10b59dfb
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Reaction notes

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