Tetrahydrofuran → 3-hydroxy-5-{[(1S)-1-(methoxymethyl)propyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548698Notes

Reaction equation

HRID 548698 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23]CC2C=CC=CC=2)[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12])[CH2:5][CH3:6].C1COCC1>[Pd].CO>[OH:23][C:21]1[CH:20]=[C:10]([CH:9]=[C:8]([O:7][C@H:4]([CH2:3][O:2][CH3:1])[CH2:5][CH3:6])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 536296563-({(1S)-1-[(methyloxy)methyl]propyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Product 1

HCID 591271273-hydroxy-5-{[(1S)-1-(methoxymethyl)propyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-({(1S)-1-[(methyloxy)methyl]propyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (4.6 g, 11 mmol) in 1:1 THF:methanol (100 mL) was added 10% w/w palladium on carbon (450 mg) and the resulting mixture was stirred under an atmosphere of hydrogen for 6 hours. The atmosphere was replaced with argon and the mixture was filtered and evaporated to afford the title compound as a white solid (3.6 g).

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-4a5e02d2b25549c5a1d1df13f5c0a53f
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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