Dimethylamine → HCID 12992938, compound

Temperature

0 °C

To a 125 mL Erlenmeyer flask equipped with a stir bar and a screw cap was added compound (ii), above, (1.48 g; 6.17 mmol) and THF (15 mL). The solution was cooled to 0° C. and triethylamine (5.16 mL; 37 mmol) and methane sulfonyl chloride (0.53 mL; 6.79 mmol) added. The reaction mixture was stirred at 0° C. for 2 h. At this point dimethylamine (2M in tetrahydrofuran)(30.8 mL; 61.7 mmol) was added and the reaction mixture heated to 70° C. for 14 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate (50 mL) and the organic phase successively washed with water (3×30 mL), brine (30 mL), dried (sodium sulfate), filtered and the solvent removed in vacuo. The crude residue was purified by column chromatography on silica gel using dichloromethane:ammonia/methanol (2N) (99:1) to yield the title compound as a brown oil (1.2 g; 73%). 13C NMR (CDCl3): δ 136.8, 128.7, 127.4, 122.6, 122.2, 115.1, 122.3, 101.6, 58.9, 45.8, and 44.8.

1. customTo a 125 mL Erlenmeyer flask equipped with a stir bar
2. customa screw cap
3. temperaturethe reaction mixture heated to 70° C. for 14 h
4. temperatureThe reaction mixture was then cooled to room temperature
5. washthe organic phase successively washed with water (3×30 mL), brine (30 mL)
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. customthe solvent removed in vacuo
9. customThe crude residue was purified by column chromatography on silica gel

ORD record

ord-63db34de81184e35a486d366c1b28308

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380242B1