1-Bromo-2-butanone → HCID 11696854, compound

HRID 2112962Notes

Reaction equation

HRID 2112962 reaction equation
[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[N:23]=[C:9]2[CH:10]=[C:11]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:13]([C:14](=[S:16])[NH2:15])[N:8]2[N:7]=1)[CH3:2].Br[CH2:26][C:27](=O)[CH2:28][CH3:29]>CCO>[CH2:1]([NH:3][C:4]([NH:5][C:6]1[N:23]=[C:9]2[CH:10]=[C:11]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[C:13]([C:14]3[S:16][CH:26]=[C:27]([CH2:28][CH3:29])[N:15]=3)[N:8]2[N:7]=1)=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 86618025HCID 86618025, compound

Product 1

HCID 11696854HCID 11696854, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the product of Step 1 (0.5 g, 1.47 mmol) and 1-bromo-2-butanone (0.22 g, 1.47 mmol) in EtOH (10 mL) was heated to reflux for 3 h. The solvent was removed under reduced pressure; the resulting yellow solid was dissolved in MeOH/CHCl3, and dried onto silica gel. The slurry was then purified by column chromatography on silica gel using 1-4% MeOH/CHCl3 as eluent, to afford 1-ethyl-3-[5-(4-ethyl-thiazol-2-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea as a solid. LCMS (APCI+) 394.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe resulting yellow solid was dissolved in MeOH/CHCl3
  5. customdried onto silica gel
  6. customThe slurry was then purified by column chromatography on silica gel using 1-4% MeOH/CHCl3 as eluent

Sources & evidence

ORD record
ord-f22d2b0efd68462b876b114b22016b27
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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