HCID 57202434, compound → HCID 57111740, compound

Temperature

80 °C

A solution of (3S-trans)-N-(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(2,3-dihydro-2-methyl-1H-isoindol-5-yl)urea (1.0 g, 1.8 mmol, compound of example 19) in acetic acid (4 mL) was treated with zinc dust (0.35 g, 5.4 mmol) under argon and heated at 80° C. for 16 hours. Additional amount (0.4 g) of zinc dust was added and the reaction mixture was heated for eight hours. It was cooled to room temperature, diluted with chloroform (100 mL) and filtered. The solvent was evaporated in vacuo and the residue was acidified with 10% hydrochloric acid (10 mL). It was then extracted with ethyl acetate and the organic extract was discarded. The acid layer was made basic (pH~11) with 10% sodium hydroxide solution, saturated with salt and extracted with chloroform (3×100 mL). The aqueous layer was filtered and the filtrate was concentrated in vacuo. The residue was diluted with 40% aqueous isopropanol. The precipitate was faltered and dried to yield the title compound (0.2 g) as a colorless solid, m.p. 215°-217° C. [αD ]25 =-13.9° (c=0.42, DMF).

1. temperaturethe reaction mixture was heated for eight hours
2. temperatureIt was cooled to room temperature
3. filtrationfiltered
4. customThe solvent was evaporated in vacuo
5. extractionIt was then extracted with ethyl acetate
6. extractionthe organic extract
7. extractionsaturated with salt and extracted with chloroform (3×100 mL)
8. filtrationThe aqueous layer was filtered
9. concentrationthe filtrate was concentrated in vacuo
10. additionThe residue was diluted with 40% aqueous isopropanol
11. customdried

ORD record

ord-8919fce3838f4583bc06f556778be464

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374643