Boron tribromide → HCID 57717495, compound

HRID 2283900Notes

Reaction equation

HRID 2283900 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:15]2=[N:16][N:17]([CH2:24][CH2:25][O:26]C)[C:18]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])=[C:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>ClCCl>[NH2:5][C:6]1[C:15]2=[N:16][N:17]([CH2:24][CH2:25][OH:26])[C:18]([CH2:19][C:20]([CH3:23])([OH:22])[CH3:21])=[C:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57717561HCID 57717561, compound

Product 1

HCID 57717495HCID 57717495, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, boron tribromide (6 mL of a 1 M solution in dichloromethane) was added to a solution of 1-[4-amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2-methylpropan-2-ol (0.500 g, 1.59 mmol) in dichloromethane (8 mL), and the reaction was stirred for four hours. The dichloromethane was removed under reduced pressure, and the residue was dissolved in a mixture of ethanol and 3 N hydrochloric acid. A solution of 7 N ammonia in methanol was added, and then the solvent was removed under reduced pressure. The treatment with ammonia and the concentration were repeated two more times. The crude product was purified by chromatography using a HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform) followed by trituration with acetonitrile and recrystallization from acetonitrile to provide 115 mg of 1-[4-amino-2-(2-hydroxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2-methylpropan-2-ol as white crystals, mp 196-198° C.

Workup

  1. customThe dichloromethane was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethanol and 3 N hydrochloric acid
  3. additionA solution of 7 N ammonia in methanol was added
  4. customthe solvent was removed under reduced pressure
  5. concentrationThe treatment with ammonia and the concentration
  6. customThe crude product was purified by chromatography
  7. washa HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform)
  8. customfollowed by trituration with acetonitrile and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-2a6987756de94d9bb50d3b706c0ca7e6
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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