4-Amino-1-methylpiperidine → N-(3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)-1-methylpiperidin-4-amine

Temperatur

80 °C

To a stirred solution of 5-(3-chlorophenyl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine (96) (50 mg, 0.137 mmol) in tert-BuOH (4 mL), 1,4 dioxane (6 mL) was added 1-methylpiperidin-4-amine (16) (14 mg, 0.23 mmol, 0.9 eq) and tert-BuOK (38 mg, 0.344 mmol, 2.5 eq). The resulting reaction mixture was degassed, purged with N2 for 10 min and Pd2(dba)3 (5 mg, 0.00549 mmol, 0.04 eq) and tertButyl X-phos (0.08 eq) was added, the mixture was degassed and purged with nitrogen for 15 min. The reaction mixture was stirred overnight at 80° C. under sealed condition for 16 h. After completion of the reaction the reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and solvent completely distilled off to get the crude. The crude was passed through 100-200 mesh silica gel. Eluting the pure compound at 5% MeOH/CHCl3 gave 25 mg of N-(3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)-1-methylpiperidin-4-amine 97.

1. customThe resulting reaction mixture
2. customwas degassed
3. custompurged with N2 for 10 min
4. customthe mixture was degassed
5. custompurged with nitrogen for 15 min
6. customunder sealed condition for 16 h
7. customAfter completion of the reaction the reaction mass
8. extractionextracted with ethyl acetate
9. dry with materialThe organic layer was dried over sodium sulphate and solvent
10. distillationcompletely distilled off
11. customto get the crude
12. washEluting the pure compound at 5% MeOH/CHCl3

ORD-Eintrag

ord-fc1d405d52ca4b71aa34d68ed98fb3e5

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09187473B2