N-bromobutanimide → HCID 21094193, compound

HRID 1350319Notes

Reaction equation

HRID 1350319 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:12]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1C(=O)N([Br:34])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:34][C:17]1[S:16][C:15]([NH:14][C:12](=[O:13])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:20][CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10408333HCID 10408333, compound

Product 1

HCID 21094193HCID 21094193, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 65, 202 mg, 510 μmol), NBS (91 mg, 510 μmol), and Bz2O2 (6 mg, 26 μmol), in CCl4 (2 mL) was heated to reflux for 16 h. After removal of the solvent, the residue was partitioned between EtOAc (30 mL) and H2O (30 mL). The organic extracts were washed with saturated aqueous NH4Cl (30 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (CH2Cl2-EtOAc, 2:3) gave the title compound: RTA=3.50 min; m/z (ES+)=516.2 [M+MeCN+H]+.

Workup

  1. temperatureto reflux for 16 h
  2. customAfter removal of the solvent
  3. customthe residue was partitioned between EtOAc (30 mL) and H2O (30 mL)
  4. washThe organic extracts were washed with saturated aqueous NH4Cl (30 mL)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationFiltration, solvent evaporation, and flash chromatography (CH2Cl2-EtOAc, 2:3)

Sources & evidence

ORD record
ord-dd6094be380b4d41a483b2f46d778433
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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