3-[(1-Methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide → 3-hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 1175854Notes

Reaction equation

HRID 1175854 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:20]CC2C=CC=CC=2)[CH:19]=1)[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=1)=[O:9])[CH3:3]>CO>[OH:20][C:18]1[CH:17]=[C:7]([CH:6]=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:19]=1)[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=1)=[O:9]

Participants

3

Reactant 1

HCID 536296253-[(1-Methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Product 1

HCID 591271833-hydroxy-5-isopropoxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[(1-Methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (51 g; 0.14 mol) was dissolved in methanol (500 mL) and THF (500 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (5.1 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off through celite, and the filtrate concentrated in vacuo. Ethyl acetate was added and filtered to give the desired compound. (30.5 g). A second crop of material was obtained in the same way (4.0 g).

Workup

  1. customTHF (500 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (5.1 g) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with nitrogen (3 times)
  8. filtrationThe catalyst was filtered off through celite
  9. concentrationthe filtrate concentrated in vacuo
  10. additionEthyl acetate was added
  11. filtrationfiltered

Sources & evidence

ORD record
ord-e4d9a06288a2437687c5be20829c89b8
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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