Boron tribromide → HCID 68952673, compound

HRID 1453854Notes

Reaction equation

HRID 1453854 reaction equation
C([O:8][C:9]1[C:10]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:11][N:12]2[CH:17]([C:18]3[N:19]=[C:20]([CH3:23])[S:21][CH:22]=3)[CH2:16][N:15]([CH3:24])[C:14](=[O:25])[C:13]=12)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:9]1[C:10]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:11][N:12]2[CH:17]([C:18]3[N:19]=[C:20]([CH3:23])[S:21][CH:22]=3)[CH2:16][N:15]([CH3:24])[C:14](=[O:25])[C:13]=12

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68952242HCID 68952242, compound

Product 1

HCID 68952673HCID 68952673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 3-(benzyloxy)-5-methyl-7-(2-methyl-1,3-thiazol-4-yl)-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (64 mg, 0.150 mmol) in anhydrous CH2Cl2 at 0° C. was added 2.0M boron tribromide in CH2Cl2 (112 μL, 0.225 mmol). The reaction was stirred at room temperature overnight, and the solvent was removed in vacuo. The resulting residue was dissolved in 0.025M H2SO4 in EtOH (1.2 mL) and heated to reflux overnight. Purification by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions afforded the title product as a viscous oil. ES MS (M+H)=337.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe resulting residue was dissolved in 0.025M H2SO4 in EtOH (1.2 mL)
  3. temperatureheated
  4. temperatureto reflux overnight
  5. customPurification by reverse phase chromatography on a C-18 column
  6. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-6aa0ba9849044545b91fe09006aa7fbc
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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