Hydrochloric Acid → HCID 23114802, compound

HRID 2080495Notes

Reaction equation

HRID 2080495 reaction equation
C(O)C.C(OC(=O)[NH:10][C:11]1[CH:16]=[C:15]([CH:17]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:14]([Br:36])=[CH:13][N:12]=1)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Br:36][C:14]1[C:15]([CH:17]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])=[CH:16][C:11]([NH2:10])=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 58734253HCID 58734253, compound

Product 1

HCID 23114802HCID 23114802, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ethanol (2 ml) solution of t-butyl[5-bromo-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]carbamate (130 mg, 0.227 mmol) was added concentrated hydrochloric acid (2 ml). The resulting mixture was stirred at room temperature for 63 hours. The reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added saturated sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was recrystallized from hexane:ethyl acetate to give the title compound (72 mg, 0.152 mmol, 67%) as a pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customTo the residue thus obtained
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-bdc56301f49f4f24b158f208bf4d956e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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