1,4-Dioxane hydrochloride → HCID 86650024, compound

HRID 1892523Notes

Reaction equation

HRID 1892523 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])=[C:14]([F:31])[CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].O1CCOCC1.[ClH:38]>ClCCl>[ClH:38].[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])=[C:14]([F:31])[CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86762010HCID 86762010, compound

Product 1

HCID 86650024HCID 86650024, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 2-[(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzyl)carbamoyl]hydrazinecarboxylate (141.6 mg, 0.314 mmol) in anhydrous dichloromethane (2 ml) was added 4M hydrogen chloride dioxane solution (2 ml). The mixture was stirred at room temperature for 2 hr, and 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 repeated 3 times to remove hydrogen chloride gas azeotropically. The residue was suspended in a mixture of ethanol (2 ml) and ethyl acetate (4 ml), filtered, washed twice with ethyl acetate, and dried under reduced pressure to give N-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzyl)hydrazinecarboxamide hydrochloride (123.6 mg, 0.319 mmol, quantitative) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate (10 ml) was added to the 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 (4 ml)
  6. filtrationfiltered
  7. washwashed twice with ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-896b229957254b51ad3f0534803f40ba
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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