Hydrazine hydrate (1:1) → 4-(4-Amino-phenyl)-1H-pyrazolo[3,4-c]pyridin-3-ylamine

HRID 1159449Notes

Reaction equation

HRID 1159449 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[N:14][CH:13]=[C:12](Cl)[C:9]=2[C:10]#[N:11])=[CH:4][CH:3]=1.O.[NH2:18][NH2:19]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:15]=[N:14][CH:13]=[C:12]3[NH:18][N:19]=[C:10]([NH2:11])[C:9]=23)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 451233613-(4-Aminophenyl)-5-chloroisonicotinonitrile

Product 1

HCID 671274914-(4-Amino-phenyl)-1H-pyrazolo[3,4-c]pyridin-3-ylamine

Procedure

The product from Example 1C (1.4 g) in hydrazine hydrate (10 mL) was heated at 110° C. for 3 hours, cooled to room temperature, and partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with 8% methanol in CH2Cl2 to provide 0.5 g of the title compound as a yellow solid. MS (ESI(+)) m/e 225 (M+H)+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 8% methanol in CH2Cl2

Sources & evidence

ORD record
ord-8812fa15ca2e4720b3569a0128ec1d38
Source dataset
uspto-grants-2010_10
Patent number
US07812166B2

Reaction notes

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