1-Butanol → 4-(4-Amino-phenyl)-1-methyl-1H-pyrazolo[3,4-c]pyridin-3-ylamine

HRID 1159451Notes

Reaction equation

HRID 1159451 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[N:14][CH:13]=C(Cl)[C:9]=2[C:10]#[N:11])=[CH:4][CH:3]=1.[CH3:17][NH:18][NH2:19].[CH2:20](O)CCC>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[N:14][CH:13]=[C:17]3[N:18]([CH3:20])[N:19]=[C:10]([NH2:11])[C:9]=23)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 6061MethylhydrazineHCID 451233613-(4-Aminophenyl)-5-chloroisonicotinonitrile

Product 1

HCID 686444744-(4-Amino-phenyl)-1-methyl-1H-pyrazolo[3,4-c]pyridin-3-ylamine

Procedure

The product from Example 1C (150 mg, 0.65 mmol) and methylhydrazine (0.35 mL) in n-butanol (2 mL) was heated in a sealed vial at 190° C. for 30 minutes with stirring in a Smith Synthesizer microwave oven (at 300W). The reaction mixture was allowed to cool to room temperature and partitioned between water and ethyl acetate. The organic extract was dried (Na2SO4), filtered, and the filtrate was concentrated to provide 0.08 g of the title compound. MS (ESI(+)) m/e 240 (M+H)+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dd4d95861b45473a84a5f97180212f45
Source dataset
uspto-grants-2010_10
Patent number
US07812166B2

Reaction notes

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