HCID 10709109, compound → HCID 10563752, compound

HRID 1838474Notes

Reaction equation

HRID 1838474 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)(=[O:11])=[O:10])[O:4][N:3]=1.[H][H]>[Pd].CO>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[O:4][N:3]=[C:2]([CH3:1])[C:6]=1[CH3:7])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 10709109HCID 10709109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10563752HCID 10563752, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 135 mg of 10% palladium on carbon in 20 mL of methanol under argon, 0.9 g (3.03 mmol) of N-(3,4-dimethyl-5-isoxazolyl)-2-nitrobenzenesulfonamide (Example 9) in 20 mL of methanol was added. The solution was hydrogenated with a balloon filled with hydrogen for 90 minutes. The mixture was filtered through Celite® and the filtrate was concentrated to afford 0.9 g of a gum. This material was chromatographed on silica initially with 9:1 methylene chloride:methanol and then with 1:1 hexanes:ethyl acetate to provide 0.2 g (24%) of Example 10 as a white solid.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c5381e8fc57a4a319658dfd12d7fad6c
Source dataset
uspto-grants-2004_01
Patent number
US06673824B1

Reaction notes

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