Acetonitrile → N-Methyl-[[4,6-bis(4-Fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]propyl]amine

HRID 2376748Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:10]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:11]2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[N:6]1.[C:34](#[N:36])C>CN.CCO>[CH3:34][NH:36][CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([N:8]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:10]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:11]2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[N:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(3-chloropropyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (0.07 g, 0.1 mmol, obtained in example 16) in acetonitrile (0.3 mL), methylamine (1.8 mL of a 33% solution in EtOH, 14.6 mmol) was added under argon atmosphere. This was heated to 60° C. for 3 days, adding methylamine (0.9 mL and 3.6 mL of a 33% solution in EtOH) after 24 and 48 h respectively. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by silica gel EtOAc-MeOH mixtures of using increasing polarity as eluent, to afford 24 mg of the title compound in solid form (yield: 29%).

Workup

dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated to dryness
customThe crude product obtained
customwas purified by silica gel EtOAc-MeOH mixtures
temperatureof using increasing polarity as eluent

Sources & evidence

ORD record: ord-5ec15e7e624e4d67a4b9f86a176f0e73
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468376B2

Reaction notes

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