Iodine → HCID 18447426, compound

A solution of iodine (0.488 g, 1.92 mmol) in hexamethyldisilane (0.560 g, 3.83 mmol) was heated at 110° C. and stirred until the purple solution became colorless. The solution was cooled to room temperature, followed by adding thereto a solution of the ethyl 3-(1H-indazol-5-ylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate (0.200 g, 0.637 mmol) obtained in Example 14 in 1,2-dichloroethane (6 ml), and the resulting mixture was heated at 50° C. and stirred for 7 hours. The mixture was cooled to room temperature and methanol was added thereto to quench the mixture. Then, the solvent was distilled off under reduced pressure and a 1N-aqueous sodium hydroxide solution was added to the residue. The solvent was distilled off under reduced pressure and the residue was dried up and then purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=100/10/1) to obtain N-(8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (0.0893 g, 58%).

1. additionby adding
2. stirringstirred for 7 hours
3. temperatureThe mixture was cooled to room temperature
4. customto quench the mixture
5. distillationThen, the solvent was distilled off under reduced pressure
6. additiona 1N-aqueous sodium hydroxide solution was added to the residue
7. distillationThe solvent was distilled off under reduced pressure
8. customthe residue was dried up
9. custompurified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=100/10/1)

ORD record

ord-922a3fcf2d6244fa9d96c9519ab98438

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2