Water → 6-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-methyl-piperidin-4-yl)-amide

温度

40 °C

To a mixture of 6-(4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (215 mg), DIPEA (313 μL) and 1-benzyl-4-methyl-piperidin-4-ylamine (175 mg) in dichloroethane (7 mL), which was being stirred at 40° C., was added BEP (200 mg). The mixture was stirred at 40° C. for 60 min, then at r.t. overnight. Water was added and the mixture was extracted with dichloromethane. To the dichloromethane phase 30% sodium methoxide in methanol (0.4 mL) was added and stirred for 30 min. The mixture was filtered and the filtrate was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed over silica (dichloromethane/methanol gradient) to give 1420 g (43%) of the title compound.

1. additionwas added BEP (200 mg)
2. stirringThe mixture was stirred at 40° C. for 60 min
3. customat r.t.
4. customovernight
5. extractionthe mixture was extracted with dichloromethane
6. additionTo the dichloromethane phase 30% sodium methoxide in methanol (0.4 mL) was added
7. stirringstirred for 30 min
8. filtrationThe mixture was filtered
9. washthe filtrate was washed with water
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated
12. customThe residue was chromatographed over silica (dichloromethane/methanol gradient)

ORDレコード

ord-7cfa41e362724d25b5e57a1ed18271f2

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08686150B2