Ethanol → HCID 68427806, compound

HRID 642567Notes

Reaction equation

HRID 642567 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[N:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[S:20][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2].[CH2:26](O)[CH3:27]>[Pd].C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:27][CH:26]=2)[C:9]2[N:18]=[C:19]([C:21]([CH3:23])([CH3:22])[CH3:24])[S:20][C:8]=2[C:7]=1[OH:25])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 68428916HCID 68428916, compound

Product 1

HCID 68427806HCID 68427806, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-tert-butyl-7-hydroxy-4-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (120 mg, 0.31 mmol) and 75 mg of 10% palladium on carbon in 6 mL of 1:10 Ethyl acetate:ethanol was placed under a hydrogen atmosphere at 20 PSI and shaken for 4 hours. The resultant mixture was filtered through a celite pad and concentrated under reduced pressure. The crude solid residue was purified by column chromatography, eluting the desired product from silica gel with a gradient of 0-30% ethyl acetate in hexanes: 75 mg of a white solid. MS (ESI+): m/z 385.0 (M+1).

Workup

  1. filtrationThe resultant mixture was filtered through a celite pad
  2. concentrationconcentrated under reduced pressure
  3. customThe crude solid residue was purified by column chromatography
  4. washeluting the desired product from silica gel with a gradient of 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-813cb3df8c0640bca3d009b600e43f65
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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