3-({(1S)-2-[(Difluoromethyl)oxy]-1-methylethyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide → 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-N-(1-methylpyrazol-3-yl)benzamide

HRID 2425495Notes

Reaction equation

HRID 2425495 reaction equation
[F:1][CH:2]([F:31])[O:3][CH2:4][C@@H:5]([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])[CH3:6]>C(O)C>[F:31][CH:2]([F:1])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([OH:23])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12])[CH3:6]

Participants

3

Reactant 1

HCID 536296413-({(1S)-2-[(Difluoromethyl)oxy]-1-methylethyl}oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide

Product 1

HCID 591271223-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-hydroxy-N-(1-methylpyrazol-3-yl)benzamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-N-(1-methylpyrazol-3-yl)-5-phenylmethoxy-benzamide (0.1 g, 0.23 mmol) was dissolved in ethanol (3 mL) and THF (3 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (0.01 g) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at RT for 20 hours until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off through celite and the filtrate concentrated in vacuo to give the desired compound (70 mg).

Workup

  1. customTHF (3 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (0.01 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

Sources & evidence

ORD record
ord-b755ca33a8e74fba966dce4c34650c02
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

Loading…