HCID 68588915, compound → HCID 59314294, compound

HRID 1047784Notes

Reaction equation

HRID 1047784 reaction equation
[CH3:1][C:2]1[C:3]([CH:23]=[CH:24][CH3:25])=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]1([C:17]([OH:19])=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:6]>CCO.[Pd]>[CH3:1][C:2]1[C:3]([CH2:23][CH2:24][CH3:25])=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]1([C:17]([OH:19])=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:6]

Participants

4

Reactant 1

HCID 68588915HCID 68588915, compound

Product 1

HCID 59314294HCID 59314294, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[3-methyl-2-(1-propenyl)-benzoylamino]-indan-2-carboxylic acid (143) (220 mg, 0.65 mmol) in absolute EtOH (10 mL) is added the catalyst, Pd—C (5 wt. % Pd, 55 mg, 2.6% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, room temperature, overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (144) as white solid (128 mg, 58%).

Workup

  1. customThe resulting reaction mixture
  2. custom50 psi, room temperature, overnight
  3. customThe catalyst is removed by the filtration through a pre-column (10 g silica gel)
  4. washwashed with EtOH
  5. concentrationThe combined solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-b0fda585aaa44ee68a68708ec17841b7
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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