1,3,5-trimethyl-1H-pyrazole-4-sulfonyl chloride → 2,8-Diazaspiro[4.5]decan-1-one

HRID 2194161Notes

Reaction equation

HRID 2194161 reaction equation
C(O)(=O)C.FC(F)(F)OC1C=CC([N:14]2[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:15]2=[O:24])=CC=1.CN1C(C)=C(S(Cl)(=O)=O)C(C)=N1>N1C=CC=CC=1>[C:15]1(=[O:24])[C:16]2([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:17][CH2:18][NH:14]1

Participants

4

Reactant 2

HCID 27373401,3,5-trimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 667873332-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one acetic acid salt

Product 1

HCID 222250112,8-Diazaspiro[4.5]decan-1-oneYield 1,167.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one acetic acid salt (0.02 g, 0.05 mmol) was dissolved in pyridine (0.5 ml) at room temperature and 1,3,5-trimethyl-1H-pyrazole-4-sulfonyl chloride (0.013 g, 0.06 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the resulting residue was dissolved in AcOEt and washed with 0.1M HCl and brine. The organic layer was dried (Na2SO4), filtered and evaporated under reduced pressure to give a crude residue which was purified by flash column chromatography (4:1 AcOEt/heptane) to yield 2-(4-trifluoromethoxy-phenyl)-8-(1,3,5-trimethyl-1H-pyrazole-4-sulfonyl)-2,8-diaza-spiro[4.5]decan-1-onel)-2,8-diaza-spiro[4.5]decan-1-one as an off-white solid (0.09 g, 31%). MS (ESI): 487.3 (MH+)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in AcOEt
  3. washwashed with 0.1M HCl and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a crude residue which
  8. customwas purified by flash column chromatography (4:1 AcOEt/heptane)

Sources & evidence

ORD record
ord-6e83412157404509addf6af05e72eb1e
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…