Bromhydrol → HCID 178454507, compound

HRID 1802431Notes

Reaction equation

HRID 1802431 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([NH:14][C:15](=[O:28])[C:16]([CH3:27])([S:18]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)(=[O:20])=[O:19])[CH3:17])=[N:12][N:13]=2)=[CH:5][CH:4]=1.[Br-].[Br-].[Br-].[Al+3]>C(S)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([NH:14][C:15](=[O:28])[C:16]([CH3:17])([S:18]([CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)(=[O:20])=[O:19])[CH3:27])=[N:12][N:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 166749BromhydrolHCID 178489123HCID 178489123, compound

Product 1

HCID 178454507HCID 178454507, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Procedure

To a solution of 118 mg (0.29 mmol) of N-[5-(4-Methoxy-phenyl)-4H-[1,2,4]triazol-3-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide in ethanethiol (5 mL) are added 750 mg (2.9 mmol) of aluminium tribromide. The reaction is stirred at room temperature for 20 h. The reaction is quenched by addition of 12M aqueous HCl solution (2 mL) and diluted with water (10 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 residual solid is washed with DCM to afford 45 mg of N-[5-(4-hydroxy-phenyl)-4H-[1,2,4]triazol-3-yl]-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide. Yield: 38%, ES-MS: m/z 395 [M+H].

Workup

  1. customThe reaction is quenched by addition of 12M aqueous HCl solution (2 mL)
  2. additiondiluted with water (10 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. washThe residual solid is washed with DCM

Sources & evidence

ORD record
ord-2ed048d9493f45daba785a6246babd3c
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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