Acetic Acid → HCID 178475035, compound

Acetic acid (0.033 g, 0.58 mmol), triethylamine (0.12 ml, 0.86 mmol), 1-hydroxybenztriazole (0.088 g, 0.65 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (0.124 g, 0.65 mmol) were added to a solution of the trans-4-(1H-indazol-5-yloxy)cyclohexanamine (0.100 g, 0.44 mmol) obtained in Example 384 in N,N-dimethylformamide (5 ml) and stirred overnight. A 2N-aqueous lithium hydroxide solution (2 ml) was added thereto and stirred for some time, and the resulting mixture was added to water and extracted three times with toluene/ethyl acetate=1/1. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the solid precipitated was suspended in a hexane/ethyl acetate mixed solvent and stirred to be washed. The solid was collected by filtration and dried under reduced pressure to obtain trans-N-[4-(1H-indazol-5-yloxy)cyclohexyl]acetamide (0.097 g, 82%).

1. stirringstirred for some time
2. extractionextracted three times with toluene/ethyl acetate=1/1
3. washThe organic layer was washed with water
4. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe solid precipitated
7. stirringstirred
8. washto be washed
9. filtrationThe solid was collected by filtration
10. customdried under reduced pressure

ORD record

ord-0762614cb4b345f4a97f453b98dedc1f

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2