Bromhydrol → HCID 135956412, compound

HRID 386903Notes

Reaction equation

HRID 386903 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[N:6][C:5]([NH:16][C:17](=[O:30])[C:18]([CH3:29])([S:20]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)(=[O:22])=[O:21])[CH3:19])=[N:4]1)[CH3:2].[Br-].[Br-].[Br-].[Al+3]>C(S)C>[CH2:1]([N:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[N:6][C:5]([NH:16][C:17](=[O:30])[C:18]([CH3:29])([S:20]([CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)(=[O:22])=[O:21])[CH3:19])=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 166749Bromhydrol2×HCID 45110760HCID 45110760, compound

Product 1

HCID 135956412HCID 135956412, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent2×

Procedure

To a solution of 446 mg (1.02 mmol) of N-[1-ethyl-5-(4-methoxy-phenyl)-1H[1,2,4]triazol-3-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide in ethanethiol (5 mL) are added 801 mg (3.01 mmol) of aluminium tribromide. The reaction is stirred at room temperature for 3 h. The reaction is quenched by addition of 6M aqueous HCl solution (2 mL). The resulting precipitate is isolated by filtration, washed with methanol and retreteated with 801 mg (3.01 mmol) of aluminium tribromide in ethanethiol (5 mL) at room temperature for further 3 h. The reaction is quenched by addition of 6M aqueous HCl solution (2 mL). The aqueous layer is extracted with ethyl acetate (3×20 mL). The combined organic extracts are dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by mass-directed preparative HPLC (neutral method) to afford 110 mg of N-[1-ethyl-5-(4-hydroxy-phenyl)-1H-[1,2,4]triazol-3-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide. Yield: 26%, ES-MS: m/z 423 [M+H].

Workup

  1. customThe reaction is quenched by addition of 6M aqueous HCl solution (2 mL)
  2. customThe resulting precipitate is isolated by filtration
  3. washwashed with methanol
  4. customThe reaction is quenched by addition of 6M aqueous HCl solution (2 mL)
  5. extractionThe aqueous layer is extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organic extracts are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by mass-directed preparative HPLC (neutral method)

Sources & evidence

ORD record
ord-11343cdb1de54fa88a4aa2682bc92510
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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