Ammonium Chloride → HCID 178507575, compound

HRID 1048809Notes

Reaction equation

HRID 1048809 reaction equation
[Cl-].[NH4+].[F:3][C:4]1[CH:5]=[C:6]([S:11][C:12]2[CH:13]=[C:14]3[C:20]([NH:21][C:22](=[O:33])[CH2:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=4)=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)[CH:7]=[C:8]([F:10])[CH:9]=1>O.C(O)C.O.C(O)(=O)C.[Fe]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C:22]([NH:21][C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([S:11][C:6]4[CH:5]=[C:4]([F:3])[CH:9]=[C:8]([F:10])[CH:7]=4)[CH:13]=3)[NH:18][N:19]=2)=[O:33])=[CH:25][CH:26]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 178520296HCID 178520296, compound

Product 1

HCID 178507575HCID 178507575, compoundYield 4.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23925IronCatalystHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 152 mg (2.72 mmol) of iron and 70 mg (1.3 mmol) of ammonium chloride in 100 μl of water is added to a solution of 0.24 g (0.544 mmol) of N-(5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-yl)-2-(4-nitrophenyl)acetamide in 10 ml of a 2:1 ethanol/water mixture. Several drops of acetic acid are added to this mixture and it is heated at 60° C. for 4 hours. After cooling and concentration of the solvents, the crude reaction product is extracted with ethyl acetate and is washed with saturated sodium bicarbonate solution. The organic phases are combined, dried on magnesium sulfate and then concentrated. The crude product is purified by silica gel chromatography (DCM/MeOH) to yield 11 mg (4%) of 2-(4-aminophenyl)-N-(5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-yl) acetamide in the form of a brown solid.

Workup

  1. temperatureAfter cooling
  2. customconcentration of the solvents, the crude reaction product
  3. extractionis extracted with ethyl acetate
  4. washis washed with saturated sodium bicarbonate solution
  5. customdried on magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-ad94bae7a70645f8a0e89bd211dea078
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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