1,8-Diazabicyclo(5.4.0)undec-7-ene → Hydrochloric Acid

HRID 244511Notes

Reaction equation

HRID 244511 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:2]([S:7]([Cl:10])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)C(=O)OC(C)(C)C)=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1>ClCCCl>[N:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][NH:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[S:11](=[O:13])(=[O:12])[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[S:7]2(=[O:9])=[O:8])=[CH:17][CH:18]=1.[ClH:10]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 246432Benzene-1,2-disulfonyl dichlorideHCID 58579582HCID 58579582, compound

Product 2

HCID 313Hydrochloric AcidHCID 46853732HCID 46853732, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 1,2-benzenedisulfonyl dichloride (72 mg, 0.26 mmol) and DCE (3 mL) at 40° C. was added a solution of tert-butyl (4-aminophenyl)(pyridin-2-ylmethyl)carbamate (78 mg, 0.26 mmol) and DBU (0.09 mL, 0.57 mmol) in dry DCE (2 mL). After 48 h, the heat was removed and the r×n was added to DCM:H2O (1:1, 5 mL) and the organic layer was separated. The aqueous layer was extracted with DCM (2×5 mL) and the collected organic layers were washed with Brine (5 mL), and dried over MgSO4. After filtration and concentration under reduced pressure, the residue was purified by preparative HPLC. The pure material was dissolved in DCM (1 mL) and 4M HCl in dioxane (0.5 mL) was added. After 3 h, the solvent was removed to provide 2-(4-((pyridin-2-ylmethyl)amino)phenyl)benzo[d][1,3,2]dithiazole 1,1,3,3-tetraoxide as an HCl Salt

Workup

  1. customthe heat was removed
  2. additionthe r×n was added to DCM:H2O (1:1, 5 mL)
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with DCM (2×5 mL)
  5. washthe collected organic layers were washed with Brine (5 mL)
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration and concentration under reduced pressure
  8. customthe residue was purified by preparative HPLC
  9. dissolutionThe pure material was dissolved in DCM (1 mL)
  10. addition4M HCl in dioxane (0.5 mL) was added
  11. waitAfter 3 h
  12. customthe solvent was removed

Sources & evidence

ORD record
ord-af522bea1fee4ba89facf0e6befca11e
Source dataset
uspto-grants-2014_02
Patent number
US08658650B2

Reaction notes

Loading…