Hydrazine → 7-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-1H-indazol-3-amine

HRID 241953Notes

Reaction equation

HRID 241953 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[C:11](F)=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])[N:7]=[C:6]2[N:19]([CH3:22])[N:20]=[CH:21][C:5]=12>C(O)CCC>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:12]3[C:11]=2[NH:2][N:1]=[C:13]3[NH2:14])[N:7]=[C:6]2[N:19]([CH3:22])[N:20]=[CH:21][C:5]=12

Participants

4

Reactant 2

HCID 9321HydrazineHCID 580832363-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-2-fluorobenzonitrile

Product 1

HCID 580832387-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-1H-indazol-3-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

Hydrazine (0.34 mL, 1.04 mmol) was added to a solution of 3-(4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)-2-fluorobenzonitrile 15 (0.030 g, 0.1046 mmol) in n-butanol and the reaction mixture was heated at 90° C. for 1 hour. The solvent was removed and diluted with ethylacetate, washed with saturated bicarbonate solution followed by brine. Drying and concentration gave 16.

Workup

  1. customThe solvent was removed
  2. additiondiluted with ethylacetate
  3. washwashed with saturated bicarbonate solution
  4. customDrying
  5. concentrationconcentration

Sources & evidence

ORD record
ord-b89673042fb84568ab134fb1ccfc6552
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

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