HCID 6482390, compound → HCID 6482396, compound

HRID 1978953Notes

Reaction equation

HRID 1978953 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:21]=[C:20]([C:22]#[C:23][CH2:24][OH:25])[S:19][C:13]=3[N:14]([CH:16]([CH3:18])[CH3:17])[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:26])[C:12]3[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][OH:25])[S:19][C:13]=3[N:14]([CH:16]([CH3:18])[CH3:17])[CH:15]=2)=[O:9])=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 6482390HCID 6482390, compound

Product 1

HCID 6482396HCID 6482396, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(4-chlorobenzyl)-2-(3-hydroxy-1-propynyl)-7-isopropyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Example No. 27) (0.225 g) in ethanol (50 mL) is hydrogenated over 10% Pd/C (68 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 recrystallized from ethyl acetate/heptane to yield 0.104 g (46%) 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 recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-bb648b58d02a49ecb34bbfcbdc72a7e9
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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