1,5-Diazabicyclo(4.3.0)non-5-ene → HCID 178490723, compound

HRID 2241169Notes

Reaction equation

HRID 2241169 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:27])[NH:25][OH:26])=[CH:20][CH:19]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1.[C:33](N1C=CN=C1)(N1C=CN=C1)=[S:34].N12CCCC1=NCCC2>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[NH:27][C:33](=[S:34])[O:26][N:25]=3)=[CH:22][CH:23]=2)=[O:16])(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 802641,1'-ThiocarbonyldiimidazoleHCID 1784907253-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide

Product 1

HCID 178490723HCID 178490723, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(5-Chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide (110 mg, 0.23 mmol) was diluted in acetonitrile (2 ml) under argon. 1,1′-Thiocarbonyldiimidazole (TCDI) (68 mg, 0.38 mmol, 1.65 equiv.) was then added, followed by 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (114 mg, 3.95 equiv.). The mixture was stirred at room temperature for 6 hours, then the solvents were evaporated. The residue was diluted with water and the pH was adjusted to 4 with HCl 1N. The aqueous phase was extracted with ethyl acetate, and the organic phase evaporated. The residue was dissolved in NaOH 1N, and washed with ether. The aqueous solution was adjusted to pH 4 with HCl 1N and then extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated. Purification via flash chromatography (dichloromethane/methanol) yielded the title compound as a light yellow solid (24 mg, 20%), MS (ISP): m/e=515.1 (M−H).

Workup

  1. customthe solvents were evaporated
  2. additionThe residue was diluted with water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. customthe organic phase evaporated
  5. dissolutionThe residue was dissolved in NaOH 1N
  6. washwashed with ether
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. customevaporated
  10. customPurification via flash chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-8deadd2ab1e94fd9b6d285c17665510b
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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