Triethylamine → HCID 58746173, compound

cis-2-Amino-cyclohexane-1-ol (85 mg, 0.56 mmol) and triethylamine (225 μl, 1.61 mmol) were dissolved in dimethylformamide (225 μl) and a solution of 5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinic acid (150 mg, 0.54 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (113 mg, 0.59 mmol) and 1-hydroxybenzotriazole (80 mg, 0.59 mmol) in dimethylformamide (5 ml) was added. The reaction was stirred under nitrogen at room temperature for 64 h and the solvent was removed under reduced pressure. The residue was partitioned between 0.5N HCl (10 ml) and ethyl acetate (10 ml) and the aqueous phase was extracted with ethyl acetate (2×10 ml). The combined organic phases were washed with brine (10 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (70:30, by volume). The product was triturated with pentane (3 ml) to give 5-fluoro-N-[cis-2-hydroxy-cyclohexyl]-2-(3-methylsulfanyl-phenoxy)-nicotinamide (118 mg) as a white solid.

1. customthe solvent was removed under reduced pressure
2. customThe residue was partitioned between 0.5N HCl (10 ml) and ethyl acetate (10 ml)
3. extractionthe aqueous phase was extracted with ethyl acetate (2×10 ml)
4. washThe combined organic phases were washed with brine (10 ml)
5. dry with materialdried over MgSO4
6. customthe solvent was removed under reduced pressure
7. customThe residue was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (70:30, by volume)
8. customThe product was triturated with pentane (3 ml)

ORD record

ord-6c995a5600674bae9e4410236b244145

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141586B2