Benzoyl Peroxide → HCID 86617363, compound

HRID 642399Notes

Reaction equation

HRID 642399 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[S:14][C:8]=2[C:7]=1[OH:27])=[O:5])[CH3:2].[Br:28]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([Br:28])[C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][N:18]([CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[S:14][C:8]=2[C:7]=1[OH:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68427358HCID 68427358, compound

Product 1

HCID 86617363HCID 86617363, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 2-(1-benzyl-1H-pyrazol-4-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester, example 91(c)(0.48 g, 1.26 mmol), N-bromosuccinimide (0.24 g, 1.32 mmol), and benzoyl peroxide (30.5 mg, 0.126 mmol) in 4.2 mL of benzene was heated at reflux temperature for 5 h. The reaction mixture was washed successively with saturated sodium bicarbonate, brine, saturated ammonium chloride solution, and brine. The organic solution was dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to produce 0.44 g of a white solid. MS: (+) m/z 459.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 5 h
  3. washThe reaction mixture was washed successively with saturated sodium bicarbonate, brine, saturated ammonium chloride solution, and brine
  4. customThe organic solution was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0008b2058ecd43418e4392a4c1106a7a
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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