Bromhydrol → HCID 178454507, compound

HRID 553644Notes

Reaction equation

HRID 553644 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-88f1c31e943b4215bce216d4a6e7e26d
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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