Water → HCID 23564383, compound

HRID 1059446Notes

Reaction equation

HRID 1059446 reaction equation
COC[N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][N:15]3[C:23]4[C:18](=[N:19][CH:20]=[N:21][C:22]=4[S:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])[N:17]=[CH:16]3)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:33]=[CH:34][CH:35]=[N:36][C:5]1=2.B(Br)(Br)Br.O>ClCCl>[N:36]1[C:5]2[NH:4][C:9]3[CH:10]=[C:11]([CH2:14][N:15]4[C:23]5[C:18](=[N:19][CH:20]=[N:21][C:22]=5[S:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[N:17]=[CH:16]4)[CH:12]=[CH:13][C:8]=3[S:7][C:6]=2[N:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23564870HCID 23564870, compound

Product 1

HCID 23564383HCID 23564383, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 15 ml of a solution of 0.109 g of ethyl 4-[7-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)purin-6-ylthio]butanoate in dichloromethane was added in a nitrogen atmosphere 0.84 ml of a 1 M solution of boron tribromide in dichloromethane and the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was distributed into dichloromethane and water. The organic layer was extracted and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) and recrystallized from diethyl ether to thereby give 40 mg of the title compound as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionThe organic layer was extracted
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-3ff7d8b501794a129c5e112f0805818d
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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