Methanol → HCID 42645776, compound

HRID 2283266Notes

Reaction equation

HRID 2283266 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[S:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([NH2:27])(=[O:26])=[O:25])(=[O:16])=[O:15])=[CH:8][CH:7]=1.CO>C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][S:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([NH2:27])(=[O:26])=[O:25])(=[O:15])=[O:16])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 42645778HCID 42645778, compound

Product 1

HCID 42645776HCID 42645776, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[[(E)-2-[4-(2-Furyl)phenyl]ethenyl]sulfonylamino]benzenesulfonamide (Example 18) (140 mg, 0.35 mmol) was dissolved in ethyl acetate (1.5 mL) and methanol (1.5 mL) and the mixture was subjected to reduction using the H-cube instrument. The reaction mixture was eluted through the Pd/C (10%) cartridge using full hydrogen (1 atm) at 0.5 ml/min. The solvent was then removed and the crude material was purified on semi-preparative HPLC using an X-Terra column to give the title compound (18 mg, 13%) as a white solid. The compound of Example 17 was also obtained.

Workup

  1. washThe reaction mixture was eluted through the Pd/C (10%) cartridge
  2. customThe solvent was then removed
  3. customthe crude material was purified on semi-preparative HPLC

Sources & evidence

ORD record
ord-44a3e100df1e49c2a0f8911a89f16539
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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