1,4-Dioxane hydrochloride → N-[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methyl}amino)benzyl]hydrazinecarboxamide dihydrochloride

To a suspension of tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methyl}amino)benzoyl]carbamoyl}hydrazinecarboxylate (306.2 mg, 0.705 mmol) in anhydrous dichloromethane (7 ml) was added 4M hydrogen chloride dioxane solution (7.0 ml, 28.0 mmol). The mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was concentrated again under reduced pressure. This operation was repeated 3 times to remove hydrogen chloride azeotropically. The residue was suspended in ethyl acetate, and the suspension was filtered, washed twice with ethyl acetate, and dried under reduced pressure. The residue was recrystallized by dissolving in methanol (3.6 ml) and then addition of ethyl acetate (12 ml). The crystals were collected by filtration, and dried under reduced pressure to give the title compound (272.8 mg, 0.670 mmol, yield 95.0%) as a white solid.

1. concentrationconcentrated under reduced pressure
2. additionEthyl acetate was added to the residue
3. concentrationthe mixture was concentrated again under reduced pressure
4. customto remove hydrogen chloride azeotropically
5. filtrationthe suspension was filtered
6. washwashed twice with ethyl acetate
7. customdried under reduced pressure
8. customThe residue was recrystallized
9. dissolutionby dissolving in methanol (3.6 ml)
10. additionaddition of ethyl acetate (12 ml)
11. filtrationThe crystals were collected by filtration
12. customdried under reduced pressure

ORD record

ord-d3e927a8c9064a90a2b13671032b7455

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2