Boron tribromide → HCID 57717553, compound

HRID 2283864Notes

Reaction equation

HRID 2283864 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:15]2=[N:16][N:17]([CH2:28][CH2:29][O:30]C)[C:18]([CH2:19][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([CH3:22])[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]([CH2:28][CH2:29][OH:30])[C:18]([CH2:19][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([CH3:21])[CH3:22])=[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 57717560HCID 57717560, compound

Product 1

HCID 57717553HCID 57717553, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 M in dichloromethane, 2.15 mL, 2.15 mmol) was added over a period of 2 minutes to a chilled (0° C.) slurry of N-{2-[4-amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (337 mg, 0.861 mmol, prepared as described in Example 592) in dichloromethane (10 mL). The reaction mixture was stirred for 14 hours and then concentrated under reduced pressure. The residue was combined with 6 M hydrochloric acid and stirred for 3 hours. The reaction mixture was diluted with 2 M aqueous sodium carbonate. The resulting precipitate was isolated by filtration and rinsed with water and chloroform. The precipitate was combined with the chloroform layer and concentrated under reduced pressure. The residue was purified by IFC (silica gel eluting with a gradient of CMA in chloroform) followed by recrystallization from ethyl acetate/hexanes/acetonitrile to provide 184 mg of N-{2-[4-amino-2-(2-hydroxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide as a white solid, mp 203-204° C. MS (ESI) m/z 378 (M+H)+; Anal. Calcd for C27H23N5O3S: C, 54.09; H, 6.14; N, 18.55. Found: C, 54.11; H, 5.97; N, 18.42.

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringstirred for 3 hours
  3. additionThe reaction mixture was diluted with 2 M aqueous sodium carbonate
  4. customThe resulting precipitate was isolated by filtration
  5. washrinsed with water and chloroform
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by IFC (silica gel eluting with a gradient of CMA in chloroform)
  8. customfollowed by recrystallization from ethyl acetate/hexanes/acetonitrile

Sources & evidence

ORD record
ord-5ec8c442fa4b4079b389afb1e24b18aa
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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