Isopropanol → HCID 178504602, compound

N-(cis-4-Hydroxymethyl-cyclohexyl)-5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinamide (120 mg, 0.307 mmol) was dissolved in a solvent mixture of isopropyl alcohol (4 ml), tetrahydrofuran (1 ml) and water (0.5 ml) and oxone™ (132 mg, 0.215 mmol) was added. The reaction was stirred at room temperature for 2 h. The reaction mixture was diluted with water (5 ml) and extracted with dichloromethane (3×10 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2 increasing to 97:3, by volume). The resulting foam was triturated with diethylether (5 ml) to give the product (108 mg) as a white solid.

1. additionwas added
2. extractionextracted with dichloromethane (3×10 ml)
3. dry with materialThe combined organic extracts were dried over MgSO4
4. customthe solvent was removed under reduced pressure
5. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (98:2 increasing to 97:3, by volume)
6. customThe resulting foam was triturated with diethylether (5 ml)

ORD record

ord-2e69842ec1aa4df8a6fe5bfd86a5fd7e

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141586B2