1,4-Dioxane hydrochloride → 2-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl hydrazinecarboxylate hydrochloride

HRID 1892492Notes

Reaction equation

HRID 1892492 reaction equation
[NH:1]([C:10]([O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[N:25]=[C:26]([NH:29][C:30](=[O:32])[CH3:31])[S:27][CH:28]=2)=[O:23])=[CH:17][CH:16]=1)=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:39]>ClCCl>[ClH:39].[NH:1]([C:10]([O:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]2[N:25]=[C:26]([NH:29][C:30](=[O:32])[CH3:31])[S:27][CH:28]=2)=[O:23])=[CH:19][CH:20]=1)=[O:11])[NH2:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 866500002-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate

Product 1

HCID 866500012-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl hydrazinecarboxylate hydrochlorideYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate (370.8 mg, 0.800 mmol) in anhydrous dichloromethane (4 ml) was added 4M hydrogen chloride dioxane solution (4 ml), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. The operation was performed twice to remove hydrogen chloride gas azeotropically. The residue was suspended in ethyl acetate, filtered, washed 3 times with ethyl acetate and 3 times with methanol, and dried under reduced pressure to give 2-[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl hydrazinecarboxylate hydrochloride (280.8 mg, 0.702 mmol, yield 87.8%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the concentrated residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customto remove hydrogen chloride gas azeotropically
  5. filtrationfiltered
  6. washwashed 3 times with ethyl acetate and 3 times with methanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9469e51b6094719830e2e18cca4a879
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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