N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenyl-1-butyn-1-yl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide → N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenylbutyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

HRID 1814896Notes

Reaction equation

HRID 1814896 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:31])[C:12]3[CH:19]=[C:18]([C:20]#[C:21][CH2:22][CH:23]([OH:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:31])[C:12]3[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][CH:23]([OH:30])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 10195313N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenyl-1-butyn-1-yl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10173959N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenylbutyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamideYield 4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenylbut-1-ynyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 88, 0.200 g) was dissolved in ethanol (60 mL) with heating and then allowed to cool to room temperature. The mixture was hydrogenated over 10% Pd/C (0.060 g) at 35 psi for 1.5 h. The reaction mixture was filtered through a Celite pad and the pad was washed with CH2Cl2 (60 mL). The filtrate was concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.008 g of the title compound as a yellow solid. Physical characteristics. 1H NMR (400 MHz, DMSO-d6) δ 10.68, 8.51, 7.40-7.30, 6.64, 5.20, 4.584.53, 4.54, 3.90, 2.75-2.72, 1.76-1.64; MS (ESI+) m/z 465 (M+H)+.

Workup

  1. temperaturewith heating
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. washthe pad was washed with CH2Cl2 (60 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2)
  6. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f4a4e421eb4b425e8c144f02de8e698d
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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