Tetrahydrofuran → N-(4-Chlorobenzyl)-1-(2-hydroxyethyl)-6-(3-hydroxypropyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067258Notes

Reaction equation

HRID 1067258 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:25][CH2:26][OH:27])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C1COCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:25][CH2:26][OH:27])[CH:11]=2)=[O:9])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 16073849N-[(4-chlorophenyl)methyl]-1-(2-hydroxyethyl)-6-(3-hydroxyprop-1-ynyl)-4-oxo-quinoline-3-carboxamide

Product 1

HCID 9931635N-(4-Chlorobenzyl)-1-(2-hydroxyethyl)-6-(3-hydroxypropyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-1-(2-hydroxyethyl)-6-(3-hydroxy-1-propynyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 5 (0.20 g) in a small amount of THF:methanol is added platinuim oxide (0.01 g). The mixture is placed under an atmosphere of hydrogen. After 2 hours, the mixture is filtered through Celite with THF:methanol washes. The filtrate is concentrated under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 4% to 16% methanol in dichloromethane. The product-containing fractions are concentrated under reduced pressure to afford 0.14 g of the title compound as a white solid.

Workup

  1. filtrationthe mixture is filtered through Celite with THF
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customchromatographed on silica eluting with 4% to 16% methanol in dichloromethane
  4. concentrationThe product-containing fractions are concentrated under reduced pressure

Sources & evidence

ORD record
ord-f48010a3f72c4a4d8a7cde9f2c4b8e03
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Reaction notes

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