N-bromobutanimide → HCID 58531057, compound

HRID 1878521Notes

Reaction equation

HRID 1878521 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)Cl.[Cl-].[NH4+]>[Br:24][C:16]1[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[N:14][N:5]2[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:7][C:2]([Cl:1])=[N:3][C:4]=12

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58531082HCID 58531082, compound

Product 1

HCID 58531057HCID 58531057, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

There was dissolved, in methylene chloride (2 mL), 5-chloro-2-(4-methyl-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (44.4 mg, 0.135 mM), then N-bromo-succinimide (27.1 mg, 0.152 mM) was added to the resulting solution and the mixture was stirred at room temperature for 40 minutes. This reaction liquid was diluted with a saturated aqueous ammonium chloride solution and then extracted with methylene chloride. The extracts thus obtained were combined, dried over anhydrous sodium sulfate, the solvent was then distilled off and the resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:10) to thus obtain the title compound (27.6 mg, yield: 50%).

Workup

  1. customThis reaction liquid
  2. extractionextracted with methylene chloride
  3. customThe extracts thus obtained
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off
  6. customthe resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:10)

Sources & evidence

ORD record
ord-25952299163d44e69303bc68d58f064c
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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