Triethylamine → HCID 69357120, compound

HRID 852660Notes

Reaction equation

HRID 852660 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8](S(CCCCl)(=O)=O)[C:9]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[CH2:22][CH3:23])(=[O:7])=[O:6].CCN(CC)CC>CCO>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[CH:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 69358903HCID 69358903, compound

Product 1

HCID 69357120HCID 69357120, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indazole-6-carboxylate (D237) (1.5 g, 3 mmol, 1 equiv) in EtOH (20 ml) was added NEt3 (920 μl, 6.6 mmol, 2.2 equiv) and the resulting solution was refluxed for 3 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with AcOEt/iso-hexane to give methyl 4-(1,1-dioxido-2-isothiazolidinyl)-1-ethyl-1H-indazole-6-carboxylate (B153) as a light brown solid which was used in the next step without further purification. [M+H]+=324.5, RT=2.35 min.

Workup

  1. temperaturethe resulting solution was refluxed for 3 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with a 2N aqueous HCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with AcOEt/iso-hexane

Sources & evidence

ORD record
ord-aafd6ca5b9e346e3a6097282b0516cc2
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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