Tetrahydrofuran → 2-Amino-4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide

HRID 1625248Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([N+:22]([O-])=O)[CH:15]=3)[N:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:3]=12.[Cl-].[NH4+].C1C[O:30]CC1>CO.O.[Fe]>[NH2:22][C:16]1[CH:15]=[C:14]([N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([Cl:1])=[C:3]3[C:10]([CH:11]([CH3:13])[CH3:12])=[N:9]2)[CH:21]=[CH:20][C:17]=1[C:18]([NH2:19])=[O:30]

Participants

Conditions

Temperature: 70 °C

Procedure

Compound (6b) (0.335 g) was dissolved in DMF (8.6 mL), and sodium hydride (0.097 g, a 55% dispersion in paraffin liquid) was added to the resulting solution at 0° C., followed by stirring for 30 min. Then, 4-fluoro-2-nitrobenzonitrile was added to the reaction solution, followed by stirring at 60° C. for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration and washed by sprinkling water to obtain 4-{4-chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.5 g, 85%). 4-{4-Chloro-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-nitrobenzonitrile (0.35 g) and ammonium chloride (0.35 g) were dissolved in a solvent mixture of THF (3 mL), methanol (3 mL), and water (3 mL). Iron (0.57 g) was added to the resulting solution, followed by stirring at 70° C. for 1 hr. Insoluble matters were filtered by celite, and the solvent was distilled away. The precipitate was washed with water and was collected by filtration to obtain compound (106a) (0.32 g, 95%) as a white solid.

Workup

filtrationInsoluble matters were filtered by celite
distillationthe solvent was distilled away
washThe precipitate was washed with water
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-42dfead1c0064d909c467105ad065137
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779142B2

Reaction notes

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