HCID 57942129, compound → HCID 57942158, compound

HRID 1898161Notes

Reaction equation

HRID 1898161 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19](=[O:30])[C:20]3[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:29])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32]>C(O)(=O)C.CCOC(C)=O.[Fe]>[NH2:26][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:29])[C:20]=1[C:19]([C:13]1[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:31]([F:34])([F:33])[F:32])[CH:4]=2)(=[O:10])=[O:9])=[CH:17][C:16]([Cl:18])=[CH:15][N:14]=1)=[O:30]

Participants

5

Reactant 1

HCID 57942129HCID 57942129, compound

Product 1

HCID 57942158HCID 57942158, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 50 mL round-bottom flask was charged with 4-chloro-N-(5-chloro-2-(2-chloro-6-nitrobenzoyl)pyridin-3-yl)-3-(trifluoromethyl)benzenesulfonamide (350 mg, 0.63 mmol), iron powder (560 mg, 10 mmol) in acetic acid (30 mL) and stirred at room temperature for 2 h and then at 50° C. for 30 min. After cooling, the reaction mixture was diluted with EtOAc, filtered through Celite and evaporated the solvent in vacuo. The residue was dissolved in EtOAc and washed with NaHCO3 (sat), brine, dried over MgSO4, and concentrated under reduced pressure and was further purified through automated normal-phase chromatography to afford the title compound: 1H NMR (400 MHz, CDCl3) δ 10.60 (s, 1H), 8.28 (d, 1H), 8.20 (d, 1H), 8.16 (d, 1H), 7.96 (dd, 1H), 7.60 (d, 1H), 7.09 (t, 1H), 6.64 (dd, 2H), 4.40 (bs, 2H); MS (ES) (M+H)+ expected 523.9. found 523.9.

Workup

  1. waitat 50° C. for 30 min
  2. temperatureAfter cooling
  3. filtrationfiltered through Celite
  4. customevaporated the solvent in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with NaHCO3 (sat), brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customwas further purified

Sources & evidence

ORD record
ord-f159f589aa954a6780373a5c930ba224
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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