HCID 67174416, compound → HCID 67311178, compound

HRID 1256067Notes

Reaction equation

HRID 1256067 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11]([NH:14][C:15]1[CH:16]=[CH:17][C:18]2[CH2:22][O:21][B:20]([OH:23])[C:19]=2[CH:24]=1)(=[O:13])=[O:12]>C(O)(=O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]3[CH2:22][O:21][B:20]([OH:23])[C:19]=3[CH:24]=2)(=[O:12])=[O:13])=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 1

HCID 67174416HCID 67174416, compound

Product 1

HCID 67311178HCID 67311178, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (0.19 g, 3.30 mmol) was added to a solution of 2-chloro-N-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-nitro-benzenesulfonamide (0.25 g, 0.67 mmol) in acetic acid (10 mL). The reaction mixture was stirred at 80° C. (bath temp) for 2 h. The mixture was then cooled to rt, and the acetic acid was removed under reduced pressure. The residue was diluted with ethyl acetate (50 mL), the undissolved particulates were removed by filtration through a pad of Celite. The filtrate was washed with water, brine and dried over Na2SO4, decanted and concentrated in vacuo. Purification was accomplished by flash silica gel column chromatography (3% methanol in dichloromethane) followed by dissolving in acidic water (with dilute HCl) and lyophilized provided 48.0 mg (21%) of the title compound as light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.10 (s, 1H), 7.63 (d, J=8.9 Hz, 1H), 7.45 (d, J=1.6 Hz, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.19 (dd, J=8.2, 1.9 Hz, 1H), 6.59 (d, J=2.2 Hz, 1H), 6.46 (dd, J=8.6, 2.2 Hz, 1H), 4.85 (s, 2H); MS (ESI) m/z=339 (M+1, positive); HPLC purity: 97.48% (MaxPlot 200-400 nm), 97.96% (220 nm).

Workup

  1. temperatureThe mixture was then cooled to rt
  2. customthe acetic acid was removed under reduced pressure
  3. additionThe residue was diluted with ethyl acetate (50 mL)
  4. customthe undissolved particulates were removed by filtration through a pad of Celite
  5. washThe filtrate was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated in vacuo
  9. customPurification
  10. dissolutionby dissolving in acidic water (with dilute HCl)

Sources & evidence

ORD record
ord-7779b85324964145a1a3282b52b8f818
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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