HCID 6482389, compound → HCID 6482394, compound

HRID 1978950Notes

Reaction equation

HRID 1978950 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:24])[C:12]3[CH:19]=[C:18]([C:20]#[C:21][CH2:22][OH:23])[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(Cl)Cl.C(O)C>C(O)C.[Pd]>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:24])[C:12]3[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][OH:23])[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6482389HCID 6482389, compoundHCID 21584144Dichloromethane ethanol

Product 1

HCID 6482394HCID 6482394, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of N-(4-chlorobenzyl)-2-(3-hydroxy-1-propynyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Example No. 24) (0.520 g) in 1/1 CH2Cl2/ethanol (160 mL) is hydrogenated over 10% Pd/C (0.156 g) 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 a pale yellow solid (this material contains a small amount of partially reduced product). This material is dissolved in ethanol (100 mL) and hydrogenated over 10% Pd/C (0.156 g) at 35 psi for 1 h. The reaction mixture is filtered through a Celite pad, and the filtrate is concentrated in vacuo. The resulting off-white solid is recrystallized from ethanol to yield 0.211 g (40%) of the desired product as an off-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
  5. customto yield a pale yellow solid (this material
  6. filtrationThe reaction mixture is filtered through a Celite pad
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe resulting off-white solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-cf0d5bb85d14449294cdab4dc1971ea6
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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