N-bromobutanimide → N-{5-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide

HRID 239273Notes

Reaction equation

HRID 239273 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:29])=[C:15]([NH:17][S:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:16]=2)=O)[CH:5]=[CH:4][N:3]=1.C1C(=O)N(Br)C(=O)C1.[CH3:38][CH:39]([CH3:43])[C:40](=[S:42])[NH2:41]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:42][C:40]([CH:39]([CH3:43])[CH3:38])=[N:41][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([F:29])=[C:15]([NH:17][S:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:16]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 109095072-MethylpropanethioamideHCID 57989679N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide

Product 1

HCID 57989776N-{5-[5-(2-Chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamideYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{5-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (1.0 g, 2.3 mmol) in DMF (10 mL) was added NBS (0.49 g, 2.8 mmol). After stirring for 45 min at rt, 2-methylpropanethioamide (0.35 g, 3.4 mmol), was added and the reaction was stirred at rt. After 4 h, the reaction mixture was partitioned between ether and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over anhydrous NaSCO4, filtered, and concentrated to generate 0.49 g (41% yield) as a yellow powder. MS (ESI) 525 (M+H).

Workup

  1. stirringthe reaction was stirred at rt
  2. waitAfter 4 h
  3. customthe reaction mixture was partitioned between ether and saturated aqueous NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous NaSCO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-742bf40e365f44ec8af62b08f41f1168
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

Loading…