N-bromobutanimide → HCID 24803617, compound

HRID 2245855Notes

Reaction equation

HRID 2245855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]3[N:23]([C:24]4[CH:28]=[CH:27][O:26][N:25]=4)[CH:22]=[N:21][N:20]=3)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].C1C(=O)N([Br:40])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:40][C:22]1[N:23]([C:24]2[CH:28]=[CH:27][O:26][N:25]=2)[C:19]([C:13]2[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:29]([F:32])([F:31])[F:30])[CH:4]=3)(=[O:9])=[O:10])=[CH:17][C:16]([Cl:18])=[CH:15][N:14]=2)=[N:20][N:21]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 59216819HCID 59216819, compound

Product 1

HCID 24803617HCID 24803617, compound

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateSolventHCID 22996148Carbon tetrachloride methylene chlorideSolvent

Procedure

4-Chloro-N-[5-chloro-2-(4-(isoxazol-3-yl)-4H-1,2,4-triazol-3-yl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide (80 mg) in CCl4/DCM (3 mL/1 mL) was charged with NBS (30 mg). The resulting mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with sat NaHCO3 and extracted EtOAc (50 mL×2), the combined organic layer was concentrated under reduced pressure. The residue was purified through automated normal-phase chromatography (10% to 100% gradient of EtOAc-Hexane), and followed by preparative HPLC (10% to 90% gradient of MeCN-water) and dried (Lyophilizer) to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 11.6 (br, 1H), 8.60 (d, 1H), 8.46 (s, 1H), 8.27 (s, 1H), 8.19 (d, 1H), 7.98 (dd, 1H), 7.62 (d, 1H), 6.63 (d, 1H). MS (ES) [M+H]+ expected 584.0, found 584.0.

Workup

  1. extractionextracted EtOAc (50 mL×2)
  2. concentrationthe combined organic layer was concentrated under reduced pressure
  3. customThe residue was purified
  4. customdried (Lyophilizer)

Sources & evidence

ORD record
ord-120d58d594734b2a92d50ba1a25f16e3
Source dataset
uspto-grants-2010_03
Patent number
US07683176B2

Reaction notes

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