HCID 59346938, compound → 3-hydroxy-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20576Notes

Reaction equation

HRID 20576 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13])C1C=CC=CC=1>C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13]

Participants

3

Reactant 1

HCID 59346938HCID 59346938, compound

Product 1

HCID 593469263-hydroxy-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(Benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (4.23 g, 0.011 mol) was dissolved in ethanol (35 mL) and THF (35 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (0.42 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 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 (2.86 g)

Workup

  1. customTHF (35 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (0.42 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-1e0a7a16fcee4a32865a787eba73ae17
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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