Water → HCID 68646408, compound

Temperature

60 °C

Of the compound from Example 160A, 243 mg (0.84 mmol) were introduced in 10 ml of acetonitrile under argon. Then at −15° C. 102 μl (1.17 mmol) of chlorosulphonyl isocyanate were added dropwise. After 30 min, the reaction solution was admixed with 20 ml of water and heated at 60° C. overnight. The reaction mixture was cooled and introduced into saturated aqueous sodium hydrogen carbonate solution. It was then extracted with ethyl acetate. The organic phase was dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. The residue was taken up in 4 ml of dichloromethane and admixed with 4 ml of a 4M solution of hydrogen chloride in dioxane. A precipitate formed immediately. After a subsequent stirring time of 10 min, the batch was freed from the solvent on a rotary evaporator. Drying in an HV gave 219 mg (77% of theory) of the title compound in 79% purity.

1. customat −15° C
2. temperatureThe reaction mixture was cooled
3. extractionIt was then extracted with ethyl acetate
4. dry with materialThe organic phase was dried over sodium sulphate
5. filtrationfiltered
6. customfreed from the solvent on a rotary evaporator
7. customA precipitate formed immediately
8. customAfter a subsequent stirring time of 10 min, the batch was freed from the solvent on a rotary evaporator
9. customDrying in an HV

ORD record

ord-29bfd0049a174293a8c2fabef45de6ec

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202895B2