HCID 10309452, compound → HCID 22498742, compound

HRID 1814892Notes

Reaction equation

HRID 1814892 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:25])[C:12]3[CH:19]=[C:18]([C:20]#[C:21][CH2:22][CH2:23][OH:24])[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:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:25])[C:12]3[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 10309452HCID 10309452, compound

Product 1

HCID 22498742HCID 22498742, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(4-Chlorobenzyl)-2-(4-hydroxybut-1-ynyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 82, 0.219 g) was dissolved in ethanol (50 mL) with heating and then allowed to cool to room temperature. The mixture was hydrogenated over 10% Pd/C (0.065 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. The resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2) to yield 0.190 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 157-160° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.69, 8.52, 7.41-7.32, 6.67, 4.55, 4.43, 3.92, 3.45-3.41, 2.74, 1.73-1.65, 1.53-1.46; 3C NMR (100 MHz, CDCl3) δ 173.6, 165.0, 155.3, 152.6, 140.4, 137.4, 132.8, 128.9, 128.6, 127.5, 116.5, 115.2, 102.7, 62.2, 43.2, 42.5, 37.7, 31.9, 27.8, 23.9; MS (ESI+) m/z 389 (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. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2)

Sources & evidence

ORD record
ord-c3e9f59533c14ccf8dee96f3426f0a8b
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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