N-bromobutanimide → HCID 118094077, compound

HRID 515538Notes

Reaction equation

HRID 515538 reaction equation
[CH:1]1([NH:6][S:7]([C:10]2[C:11]3[CH:12]=[CH:13][C:14](=[O:27])[NH:15][C:16]=3[CH:17]=[C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:19]=2)(=[O:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:35])C(=O)C1>>[Br:35][C:13]1[C:14](=[O:27])[NH:15][C:16]2[CH:17]=[C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:19]=[C:10]([S:7]([NH:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)(=[O:9])=[O:8])[C:11]=2[CH:12]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 118094069HCID 118094069, compound

Product 1

HCID 118094077HCID 118094077, compound

Procedure

A solution of N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2-dihydroquinoline-5-sulfonamide (100 mg, 0.26 mmol) and NBS (150 mg, 3 equiv) was heated at 80° C. for 1 hour. The reaction mixture was partitioned between aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and purified on silica gel (rf=0.75 in ethyl acetate) to give 3-bromo-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2-dihydroquinoline-5-sulfonamide as a white powder.

Workup

  1. customThe reaction mixture was partitioned between aqueous sodium bicarbonate solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. custompurified on silica gel (rf=0.75 in ethyl acetate)

Sources & evidence

ORD record
ord-4fe6297ff8ed429a9700f702f10fe40b
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

Loading…