Water → HCID 68646379, compound

Temperature

-10 °C

Of the compound from Example 172A, 242 mg (0.86 mmol) were introduced in 12 ml of acetonitrile under argon, and admixed dropwise at −15° C. with 105 μl (1.20 mmol) of chlorosulphonyl isocyanate. The reaction mixture was stirred at −10° C. for 30 minutes. Then 12 ml of water were added and the mixture was stirred at 60° C. overnight. The reaction mixture was cooled, rendered basic using saturated aqueous sodium hydrogen carbonate solution and extracted with three times 10 ml of ethyl acetate. The organic phases were combined, dried over magnesium sulphate, filtered and freed from the solvent on a rotary evaporator. The residue was admixed with 6 ml of a 4M solution of hydrogen chloride in dioxane, the components were stirred together for 10 minutes, and the mixture was concentrated on a rotary evaporator. The residue was dried in an HV. This gave 186 mg (83% of theory) of the title compound.

1. stirringthe mixture was stirred at 60° C. overnight
2. temperatureThe reaction mixture was cooled
3. extractionextracted with three times 10 ml of ethyl acetate
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. customfreed from the solvent on a rotary evaporator
7. stirringthe components were stirred together for 10 minutes
8. concentrationthe mixture was concentrated on a rotary evaporator
9. customThe residue was dried in an HV

ORD record

ord-f82420dd3e0a4e54b904f3019166fcef

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202895B2