Hydrazine hydrate (1:1) → HCID 178509244, compound

HRID 1048784Notes

Reaction equation

HRID 1048784 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[N:12]=[C:11]([S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>C(O)CC>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[S:13][C:11]1[N:12]=[C:5]2[NH:2][N:3]=[C:7]([NH2:8])[C:6]2=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866805632-Chloro-6-(2,4-difluorophenylthio)nicotinonitrile

Product 1

HCID 178509244HCID 178509244, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

0.561 mL (11.57 mmol) of hydrazine monohydrate is added under nitrogen to a stirring solution of 1.09 g (3.86 mmol) of 2-chloro-6-(2,4-difluorophenylthio)nicotinonitrile in 15 mL of propanol. The reaction medium is heated at 80° C. for 4 hours. A precipitate is obtained when the reaction medium is returned to room temperature. This precipitate is filtered and rinsed with ethanol. The solid is dissolved in an ethyl acetate fraction and washed with a 1N HCl solution. The organic phase is dried on magnesium sulfate and dry evaporated to yield 420 mg (39%) of 6-(2,4-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-amine in the form of a yellow solid.

Workup

  1. customA precipitate is obtained when the reaction medium
  2. customis returned to room temperature
  3. filtrationThis precipitate is filtered
  4. washrinsed with ethanol
  5. dissolutionThe solid is dissolved in an ethyl acetate fraction
  6. washwashed with a 1N HCl solution
  7. customThe organic phase is dried on magnesium sulfate
  8. customdry
  9. customevaporated

Sources & evidence

ORD record
ord-a229ffe37f5f4a048a097ac2cf310480
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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