1,4-Dioxane hydrochloride → N-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)hydrazinecarboxamide trihydrochloride

HRID 1465480Notes

Reaction equation

HRID 1465480 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:36]=[CH:35][C:21]([CH2:22][NH:23][C:24]([NH:26][NH:27]C(OC(C)(C)C)=O)=[O:25])=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O1CCOCC1.[ClH:43]>O1CCOCC1>[ClH:43].[ClH:43].[ClH:43].[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:36]=[CH:35][C:21]([CH2:22][NH:23][C:24]([NH:26][NH2:27])=[O:25])=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58181223Tert-butyl 2-[(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate

Product 1

HCID 67266593N-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)hydrazinecarboxamide trihydrochlorideYield 90.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of tert-butyl 2-[(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate (121.0 mg, 0.243 mmol) in anhydrous dioxane (1.2 ml) was added 4M hydrogen chloride dioxane solution (1.2 ml). After stirring at room temperature for 5 hrs, the reaction mixture was concentrated under reduced pressure. Ethyl acetate (10 ml) was added to the residue, and the mixture was concentrated again under reduced pressure. This operation was performed 3 times to azeotropically remove hydrogen chloride gas. The residue was suspended in a mixture of ethanol (3 ml) and ethyl acetate (6 ml), filtered, washed with ethyl acetate and dried under reduced pressure to give the title compound (111.0 mg, yield 90.1%) as a slightly yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate (10 ml) was added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. additionThe residue was suspended in a mixture of ethanol (3 ml) and ethyl acetate (6 ml)
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-9309e39ea29346b19d937a61290bc583
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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