Acetohydroxamic Acid → 7-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine

HRID 241954

Reaction equation

HRID 241954 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2C(F)=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12.C([NH:24]O)(=O)C.[C:26](=[O:29])([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:26]3[O:29][N:24]=[C:11]([NH2:12])[C:10]=3[CH:13]=[CH:14][CH:15]=2)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12

Participants

5

Reactant 3

HCID 1990Acetohydroxamic Acid2×HCID 11430Potassium CarbonateHCID 58083236HCID 58083236, compound

Product 1

HCID 580832327-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-2-fluorobenzonitrile 15 (90 mg, 0.299 mmol) was added to a mixture of acetohydroxamic acid, CH3C(O)NHOH (0.0675 g, 0.899 mmol) and potassium carbonate (0.145 g, 1.049 mmol) in 4 mL dimethylformamide and the resultant reaction mixture was heated for 2 hours at 50° C. The solvent was removed, diluted with ethyl acetate and washed with saturated sodium bicarbonate (1×20 mL) followed by brine (1×20 mL), dried over anhydrous sodium sulfate, concentrated and purified by a Biotage purification system eluting with ethyl acetate and hexanes to obtain 17 (35 mg, 40%).

Workup

  1. customthe resultant reaction mixture
  2. customThe solvent was removed
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate (1×20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by a Biotage purification system
  8. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-234f3f97ed2e43b4a692471e1070693d
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Linked notes

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