HCID 9844719, compound → HCID 10047672, compound

HRID 2299298Notes

Reaction equation

HRID 2299298 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[CH:20]=[C:19]([C:21]#[C:22][CH2:23][CH2:24][OH:25])[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1>[Pd].C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[S:18][C:13]=3[N:14]([CH2:16][CH3:17])[CH:15]=2)=[O:9])=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 9844719HCID 9844719, compound

Product 1

HCID 10047672HCID 10047672, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of N-(4-chlorobenzyl)-7-ethyl-2-(4-hydroxy-1-butynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Example No. 15) (0.257 g) in 1/1 CH2Cl2/CH3OH (50 mL) is hydrogenated over 10% Pd/C (75 mg) at 35 psi for 2 h. The reaction mixture is filtered through a Celite pad, and the filtrate is concentrated in vacuo. The resulting pale yellow solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.209 g (81%) of the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture is filtered through a Celite pad
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe resulting pale yellow solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2da88119312140a0ae01e90e59471992
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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