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

HRID 1892519Notes

Reaction equation

HRID 1892519 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:30]=[CH:29][C:15]([CH2:16][NH:17][C:18]([NH:20][NH:21]C(OC(C)(C)C)=O)=[O:19])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].O1CCOCC1.[ClH:37]>ClCCl>[ClH:37].[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:30]=[CH:29][C:15]([CH2:16][NH:17][C:18]([NH:20][NH2:21])=[O:19])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86650019Tert-butyl 2-[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate

Product 1

HCID 86650020N-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)hydrazinecarboxamide hydrochlorideYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 2-[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate (281.8 mg, 0.65 mmol) in anhydrous dichloromethane (3.25 ml) was added 4M-hydrogen chloride dioxane solution (3.25 ml, 13.0 mmol). After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was concentrated again under reduced pressure. The operation was performed 3 times to remove hydrogen chloride gas azeotropically. The residue was suspended in ethyl acetate and filtered. The filtered product was washed with ethyl acetate, and dried under reduced pressure to give the title compound (245.1 mg, quantitative) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated 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 gas azeotropically
  5. filtrationfiltered
  6. washThe filtered product was washed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-1bed74c434a245de8a813303a37e9859
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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