Nitrogen → 2-Cyclohexyl-8-ethenesulfonyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one

HRID 1754927Notes

Reaction equation

HRID 1754927 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].Cl.Cl.[CH:10]1([C:16]2[NH:20][C:19](=[O:21])[C:18]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:17]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C.N#N>C(Cl)Cl>[CH:10]1([C:16]2[NH:20][C:19](=[O:21])[C:18]3([CH2:22][CH2:23][N:24]([S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])[CH2:25][CH2:26]3)[N:17]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 668181022-Cyclohexyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one dihydrochloride

Product 1

HCID 668163772-Cyclohexyl-8-ethenesulfonyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-ethanesulfonyl chloride (440 μl, 4.21 mmol) was added to a solution of 2-cyclohexyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one dihydrochloride (1.50 g, 3.24 mmol) and triethylamine (2.7 ml, 19.4 mmol) in CH2Cl2 (30 ml) at room temperature in an N2 atmosphere. The mixture was stirred at room temperature for 30 minutes, and then washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was triturated with AcOEt-hexane, and the solid was then collected by filtration and dried to give 2-cyclohexyl-8-ethenesulfonyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one as a colorless solid (692 mg, 66%).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was triturated with AcOEt-hexane
  5. filtrationthe solid was then collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-d97f3d53c79047a893135f07a349d54f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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