HCID 53629666, compound → 3-Hydroxy-N-(5-methylpyrazin-2-yl)-5-[(propan-2-yl)oxy]benzamide

HRID 1011766Notes

Reaction equation

HRID 1011766 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([O:21]CC2C=CC=CC=2)[CH:20]=1)[C:8]([NH:10][C:11]1[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][N:12]=1)=[O:9])[CH3:3]>[Pd].C(O)C.C1COCC1>[OH:21][C:19]1[CH:18]=[C:7]([CH:6]=[C:5]([O:4][CH:2]([CH3:3])[CH3:1])[CH:20]=1)[C:8]([NH:10][C:11]1[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][N:12]=1)=[O:9]

Participants

5

Reactant 1

HCID 53629666HCID 53629666, compound

Product 1

HCID 591271623-Hydroxy-N-(5-methylpyrazin-2-yl)-5-[(propan-2-yl)oxy]benzamideYield 81.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on charcoal (550 mg) was added to a solution of 3-[(1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)-5-[(phenylmethyl)oxy]benzamide (5.5 g, 14.6 mmol) in ethanol (75 mL) and THF (50 mL) and the mixture stirred at RT under a hydrogen atmosphere for 24 hours. The catalyst was removed by filtration and the filtrates evaporated in vacuo to a residue which was crystallised from ethyl acetate to give the desired compound (3.42 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrates evaporated in vacuo to a residue which
  3. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-3094f0c0b5714210ac33a7b2c8c4c9db
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

Loading…