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

HRID 1892482Notes

Reaction equation

HRID 1892482 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:16][C:15]=1[F:31])=[O:11])[NH:2]C(OC(C)(C)C)=O.O1CCOCC1.[ClH:38]>ClCCl>[ClH:38].[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:16][C:15]=1[F:31])=[O:11])[NH2:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 866499894-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzyl tert-butyl hydrazine-1,2-dicarboxylate

Product 1

HCID 866499904-{2-[2-(Acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzyl hydrazinecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzyl tert-butyl hydrazine-1,2-dicarboxylate (147.0 mg, 0.325 mmol) in anhydrous dichloromethane (2 ml) was added 4M hydrogen chloride dioxane solution (2 ml). After stirring at room temperature for 2 hr, and the mixture was concentrated under reduced pressure. Ethyl acetate was added to the concentrated residue, and the mixture was concentrated again under reduced pressure. This operation was performed 3 times to remove hydrogen chloride gas azeotropically. The residue was suspended in a mixture of ethanol (2 ml) and ethyl acetate (8 ml) and filtered. The filtered product was washed twice with ethyl acetate, and dried under reduced pressure to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzyl hydrazinecarboxylate hydrochloride (129.1 mg, quantitative) as a white solid.

Workup

  1. concentrationthe 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. additionThe residue was suspended in a mixture of ethanol (2 ml) and ethyl acetate (8 ml)
  6. filtrationfiltered
  7. washThe filtered product was washed twice with ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a651eb0332a546309910cf949674497e
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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