Sodium Hydroxide → HCID 178431630, compound

Under a nitrogen atmosphere, 28%-sodium methoxide (64 μl, 0.311 mmol) was added at 0° C. to a suspension of cis-1-{4-[(1-acetyl-4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}pyrrolidine-2,5-dione (500 mg, 0.311 mmol) in a mixture of methanol (3 ml) and tetrahydrofuran (3 ml). After 10 minutes, a saturated aqueous ammonium chloride solution was added to the reaction solution and the resulting mixture was poured into water and extracted with ethyl acetate. The extract solution was concentrated under reduced pressure, and to a solution of the resulting residue in tetrahydrofuran (4 ml) was added lithium aluminum hydride (47 mg, 1.25 mmol) and the resulting mixture was refluxed. After 4 hours, water, a 2M-aqueous sodium hydroxide solution and water were added thereto in that order, and the resulting mixture was filtered by the use of Celite. The filtrate 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 cis-4-methyl-5-[(4-pyrrolidin-1-ylcyclohexyl)oxy]-1H-indazole (59.6 mg, 64%) and cis-4({4-methyl-1H-indazol-5-yl}oxy)cyclohexyl}amino)butan-1-ol (15.4 mg, 16%).

1. extractionextracted with ethyl acetate
2. concentrationThe extract solution was concentrated under reduced pressure
3. temperaturethe resulting mixture was refluxed
4. waitAfter 4 hours
5. filtrationin that order, and the resulting mixture was filtered by the use of Celite
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia))

ORD record

ord-0670548a7c054c4786497a5f9f60f18c

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2