N-bromobutanimide → HCID 86704188, compound

HRID 1497651Notes

Reaction equation

HRID 1497651 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[S:11][CH:12]=2)=[C:6]([F:20])[CH:5]=[CH:4][C:3]=1[NH:21][S:22]([C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[F:32])(=[O:24])=[O:23].[Br:33]N1C(=O)CCC1=O>C(Cl)Cl>[Br:33][C:12]1[S:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[N:9][C:8]=1[C:7]1[C:2]([F:1])=[C:3]([NH:21][S:22]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])(=[O:23])=[O:24])[CH:4]=[CH:5][C:6]=1[F:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68285123HCID 68285123, compound

Product 1

HCID 86704188HCID 86704188, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg (0.31 mmol) of N-{2,4-Difluoro-3-[2-(4-methyl-piperazin-1-yl)-thiazol-4-yl]-phenyl}-2,5-difluoro-benzenesulfonamide were suspended in 15 mL of dry DCM and 103 mg (0.62 mmol) of N-bromosuccinimide were added. The reaction was maintained at r.t. for 1 h then diluted with the same solvent and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated. The residue was triturated with petroleum ether and filtered, to afford 128 mg (73%) of N-{3-[5-bromo-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]-2,4-difluorophenyl}-2,5-difluorobenzenesulfonamide.

Workup

  1. additionthen diluted with the same solvent
  2. washwashed with aqueous NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with petroleum ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7e5f2b0a8ff04027ae9f02738ffde6cf
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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