Sodium triacetoxyborohydride → N1-Methyl-5-(2-(((4-(azetidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide

Azetidine hydrochloride (179 mg, 2.00 mmol) and sodium triacetoxyborohydride (434 mg, 2.05 mmol) were added to a dichloromethane (3.7 ml) solution of N1-methyl-5-(2-(4-oxopiperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide (555 mg, 1.36 mmol) synthesized in Example 40, and stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure; and the residue was purified by use of silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol system). The resultant was washed with a solvent mixture of ether-hexane=1:1; and the solid was filtered off to yield crystals of the title compound (5 mg), and a mixture (410 mg) including the title compound.

1. customThe reaction mixture was partitioned between ethyl acetate and water
2. dry with materialand the organic layer was dried over anhydrous sodium sulfate
3. concentrationThe solution was concentrated under reduced pressure
4. customand the residue was purified by use of silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol system)
5. washThe resultant was washed with a solvent mixture of ether-hexane=1:1
6. filtrationand the solid was filtered off

ORD record

ord-d39c1c87a7ec44269356f1fc09d13d0e

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109219B2