Ammonium Chloride → HCID 16753850、化合物

To a solution of 4-fluoro-2-(methylthio)benzoic acid (8.1 g, 43.6 mmol) in degassed DMF (100 mL) under nitrogen was added ammonium chloride (4.66 g, 87.2 mmol) followed by 1-hydroxy-7-azabenzotriazole (11.87 g, 87.2 mmol) and N,N,N-diisopropylethylamine (30.38 mL, 174.4 mmol). To this mixture was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and the reaction was stirred for 16 hour. LCMS analysis indicated that the reaction was complete. The DMF was removed in vacuo and the residue was partitioned between methylene chloride (800 mL) and 5% aqueous HCl (400 mL). The organic phase was washed with water (400 mL), saturated sodium bicarbonate solution (400 mL), and brine (400 mL). The organics were dried over Na2SO4, filtered, and reduced to a small volume in vacuo. The product crystallized upon solvent reduction. The crystals were filtered and dried iii vacuo to afford the title compound.

1. customThe DMF was removed in vacuo
2. customthe residue was partitioned between methylene chloride (800 mL) and 5% aqueous HCl (400 mL)
3. washThe organic phase was washed with water (400 mL), saturated sodium bicarbonate solution (400 mL), and brine (400 mL)
4. dry with materialThe organics were dried over Na2SO4
5. filtrationfiltered
6. customThe product crystallized upon solvent reduction
7. filtrationThe crystals were filtered
8. dry with materialdried iii vacuo

ORDレコード

ord-da4c74d5e5d14d5abbfe5ccb894131f7

出典データセット

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07279487B2