HCID 22498763, compound → HCID 22498716, compound

HRID 1814893Notes

Reaction equation

HRID 1814893 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:19]=[C:18]([C:20]#[C:21][CH2:22][CH2:23][CH2:24][OH:25])[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:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22498763HCID 22498763, compound

Product 1

HCID 22498716HCID 22498716, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(4-Chlorobenzyl)-2-(5-hydroxypent-1-ynyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 84, 0.125 g) was dissolved in ethanol (40 mL) with heating and then allowed to cool to room temperature. The mixture was hydrogenated over 10% Pd/C (0.038 g) at 35 psi for 2 h. The reaction mixture was filtered through a Celite pad and the pad was washed with CH2Cl2 (75 mL). The filtrate was concentrated in vacuo and then resubjected to the reaction conditions for 1 h. The resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2) followed by recrystallization from ethyl acetate to yield 0.061 g of the title compound as a white solid. Physical characteristics. M.p. 151-152° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.69, 8.51, 7.41-7.32, 6.67, 4.54, 4.37, 3.92, 3.41-3.37, 2.73, 1.68-1.63, 1.49-1.42, 1.40-1.33; MS (ESI+) m/z 403 (M+H)+.

Workup

  1. temperaturewith heating
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. washthe pad was washed with CH2Cl2 (75 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customresubjected to the reaction conditions for 1 h
  6. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f9e99bb9cf064815833a602165916f1c
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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