Hydrochloric Acid → 6-[(4-Chlorobenzene-1-sulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-amine

HRID 2080444Notes

Reaction equation

HRID 2080444 reaction equation
C(O)C.C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([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])[N:12]=1)(C)(C)C.Cl>C(OCC)(=O)C>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([S:26]([CH:17]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:13]2[N:12]=[C:11]([NH2:10])[CH:16]=[CH:15][CH:14]=2)(=[O:28])=[O:27])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 58734259HCID 58734259, compound

Product 1

HCID 231147766-[(4-Chlorobenzene-1-sulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-amineYield 71.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ethanol (5 ml) solution of t-butyl[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]carbamate (370 mg, 0.748 mmol) was added concentrated hydrochloric acid (5 ml). The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture was washed sequentially with saturated sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (210 mg, 0.537 mmol, 71%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customTo the residue thus obtained
  3. washThe resulting mixture was washed sequentially with saturated sodium bicarbonate and brine
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1bebf0f496f423280319a2e0b3271ea
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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