Thiazole-5-carbohydrazide → HCID 66599375, compound

4-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37) (263 mg, 0.903 mmol) was suspended in dichloromethane (DCM) (2 mL) before treating with triethyloxonium tetrafluoroborate (189 mg, 0.994 mmol) and stirring for 45 mins at RT under argon before adding 1,3-thiazole-5-carbohydrazide (I109)(155 mg, 1.084 mmol) and stirring for 18 hours (overnight). The DCM was removed and the residue was suspended in 1-butanol (2.0 mL) and heated at 110° C. for 3 hours. The reaction was cooled to RT, diluted with DCM (30 ml) and washed with saturated sodium bicarbonate solution (20 ml). The aqueous layers were extracted with DCM (2×20 ml), combined, washed with brine (20 ml), dried (MgSO4), filtered and evaporated to afford a yellow gum of crude product which was purified by MDAP. Desired fractions were isolated and solvent evaporated to afford a colourless gum which solidified when triturated with Et2O to afford a pale yellow solid of desired product in 100 mg.

1. stirringstirring for 18 hours (overnight)
2. customThe DCM was removed
3. temperatureheated at 110° C. for 3 hours
4. temperatureThe reaction was cooled to RT
5. additiondiluted with DCM (30 ml)
6. washwashed with saturated sodium bicarbonate solution (20 ml)
7. extractionThe aqueous layers were extracted with DCM (2×20 ml)
8. washwashed with brine (20 ml)
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. customevaporated
12. customto afford a yellow gum of crude product which
13. customwas purified by MDAP
14. customDesired fractions were isolated
15. customsolvent evaporated
16. customto afford a colourless gum which
17. customtriturated with Et2O

ORD record

ord-4864f55f944045cabeeb3324028af4d2

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2