Ammonium Chloride → HCID 178507575, compound

HRID 334443Notes

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

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

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

Sources & evidence

ORD record: ord-1776c875352042cc97e4e1bd55281e9e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883821B2

Reaction notes

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