HCID 66681065, compound → HCID 66681593, compound

HRID 1964660Notes

Reaction equation

HRID 1964660 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:38])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([O:30]CC3C=CC=CC=3)=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:11]=1>CO.[C].[Pd]>[CH3:1][O:2][CH2:3][C@H:4]([CH3:38])[O:5][C:6]1[CH:7]=[C:8]([C:23]2[NH:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=2)[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][N:14]=2)[CH:11]=1

Participants

4

Reactant 1

HCID 66681065HCID 66681065, compound

Product 1

HCID 66681593HCID 66681593, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Benzyl 5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrole-2-carboxylate (3.58 g, 6.66 mmol) synthesized in Example (97d) was dissolved in methanol (100 mL), and a 10% palladium carbon catalyst (2.00 g) was added, followed by stirring at room temperature for 3 hours under hydrogen atmosphere. The palladium carbon catalyst was removed by Celite filtration, followed by washing with tetrahydrofuran. The solvent was distilled off under reduced pressure to afford the desired compound (2.56 g, 86%) as a white solid.

Workup

  1. customThe palladium carbon catalyst was removed by Celite filtration
  2. washby washing with tetrahydrofuran
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ce82f1cb57f64540a531b571e3ee426a
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

Loading…