HCID 178418361, compound → HCID 178462954, compound

HRID 2301993Notes

Reaction equation

HRID 2301993 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH2:27])=[NH:26])[CH:18]=2)[CH:13]=[C:12]([CH2:28][C:29]([OH:31])=[O:30])[C:11]1=[O:32])[CH3:9].[H][H]>CO.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH2:27])=[NH:26])[CH:18]=2)[CH2:13][CH:12]([CH2:28][C:29]([OH:31])=[O:30])[C:11]1=[O:32])[CH3:9]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178462953HCID 178462953, compound

Product 1

HCID 178462954HCID 178462954, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [1-ethyl-7-(3-guanidino-propoxy)-2-oxo-1,2-dihydro-quinolin-3-yl]-acetic acid trifluoroacetate (400 mg, 0.87 mmol) in 20 ml of methyl alcohol and 0.4 g of 10% Pd/C was hydrogenated under 50 psi of hydrogen for 3 days. The reaction mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo to a residue which was dissolved in 10 ml of hot acetic acid and hydrogenated over 0.4 g of 10% Pd/C for 3 days. The reaction mixture was filtered through diatomaceous earth and the filter cake washed with hot methyl alcohol. The combined filtrates were evaporated in vacuo to a residue of oil and solid. The residue was purified by chromatography on a reverse phase column to afford 57 mg of the title compound as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo to a residue which
  3. dissolutionwas dissolved in 10 ml of hot acetic acid
  4. filtrationThe reaction mixture was filtered through diatomaceous earth
  5. washthe filter cake washed with hot methyl alcohol
  6. customThe combined filtrates were evaporated in vacuo to a residue of oil and solid
  7. customThe residue was purified by chromatography on a reverse phase column

Sources & evidence

ORD record
ord-3847a42be3514381abc1b41ad30ef845
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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