Acetic Acid → HCID 18447196, compound

The 5-(piperidin-4-yloxy)-1H-indazole (80 mg, 0.368 mmol) obtained in Example 42 was suspended in methanol (2 ml), and acetone (0.031 ml, 1.10 mmol) and acetic acid (0.105 ml, 1.84 mmol) were added dropwise thereto. Then, sodium cyanoborohydride (116 mg, 1.84 mmol) was added thereto. After 18 hours, acetone, acetic acid and sodium cyanoborohydride were further added in the same amounts, respectively, as above. After 3 days, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the resulting mixture was poured into water (20 ml) and extracted with chloroform (20 ml×3). The organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia)) to obtain 5-[(1-isopropylpiperidin-4-yl)oxy]-1H-indazole (30 mg, 31%).

1. waitAfter 3 days
2. extractionextracted with chloroform (20 ml×3)
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. customThe organic layer dried
5. concentrationwas concentrated under reduced pressure
6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia))

ORD record

ord-49f4443144c3408faa679203f84ad9b0

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2