Water → HCID 66611679, compound

Temperature

60 °C

A solution of 350 mg (1.10 mmol) of the compound of Example 17A in 50 ml of acetonitrile was cooled to −15° C., and a solution of 191 μl (2.19 mmol) of chlorosulphonyl isocyanate in 10 ml of acetonitrile was added dropwise. After 5 min, 50 ml of water were added and the mixture was heated at 60° C. for 4 h. After cooling to RT, 50 ml of a saturated aqueous sodium bicarbonate solution were added and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the volatile components on a rotary evaporator. 5 ml of a 4 N solution of hydrogen chloride in dioxane were added to the residue, and the mixture was stirred for 5 min Once more, the volatile components were then removed on a rotary evaporator. The residue (385 mg) corresponded to the crude title compound in a purity of about 60% according to LC/MS (about 70% of theory); this material was reacted further without purification.

1. temperatureAfter cooling to RT
2. extractionthe mixture was extracted three times with ethyl acetate
3. dry with materialThe combined organic phases were dried over sodium sulphate
4. customfreed from the volatile components on a rotary evaporator
5. addition5 ml of a 4 N solution of hydrogen chloride in dioxane were added to the residue
6. customthe volatile components were then removed on a rotary evaporator
7. customthis material was reacted further without purification

ORD record

ord-a4a402d9e2824d95928f6dcbff7a71ba

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09180120B2