Acetic Acid → N1-Methyl-5-(2-(((4-(morpholin-4-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide

Morpholine (228 mg, 1.64 mmol), sodium triacetoxyborohydride (372 mg, 1.76 mmol), and acetic acid (0.134 ml, 2.34 mmol) were added to a dichloromethane (3.5 ml) solution of N1-methyl-5-(2-(4-oxopiperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide (476 mg) 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 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 the title compound (110 mg) as crystals.

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 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-e5bae11cbfae442a965b0d68abfefc4a

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109219B2