Methanol → HCID 9931409, compound

HRID 1067978Notes

Reaction equation

HRID 1067978 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]([CH:25]3[CH2:27][CH2:26]3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.CO>C1COCC1>[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]([CH2:21][CH2:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH:25]3[CH2:27][CH2:26]3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 16073845HCID 16073845, compound

Product 1

HCID 9931409HCID 9931409, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-1-cyclopropyl-6-(3-hydroxy-1-propynyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.17 g) from Example No. 25 in THF (3 mL) and methanol (3 mL) is added platinuim oxide (0.01 g). The mixture is placed under an atmosphere of hydrogen gas. After 1 hour, 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 2% to 4% methanol in dichloromethane. The product-containing fractions are concentrated under reduced pressure to afford 0.13 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 2% to 4% methanol in dichloromethane
  4. concentrationThe product-containing fractions are concentrated under reduced pressure

Sources & evidence

ORD record
ord-eba67d352168413da49378d669450203
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

Loading…