N,N'-Dimethylethylenediamine → HCID 59577888, compound

HRID 2194123Notes

Reaction equation

HRID 2194123 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4I)(=[O:21])=[O:20])[CH2:15][CH2:14]3)[C:10]2=[O:29])=[CH:5][CH:4]=1)[CH3:2].[NH:30]1[CH2:34][CH2:33][CH2:32][C:31]1=[O:35].C([O-])([O-])=O.[K+].[K+].CNCCNC>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])(=[O:21])=[O:20])[CH2:15][CH2:14]3)[C:10]2=[O:29])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 49804518HCID 49804518, compound2×

Product 1

HCID 59577888HCID 59577888, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-ethyl-phenyl)-8-(2-iodo-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.06 g), compound of example 74), 2-pyrrolidinone (0.015 g), K2CO3 (0.055 g) and N,N′-dimethylethylenediamine (0.015 g) was heated in DMF under an argon atmosphere for 24 h at 150° C. The mixture was then cooled to RT and extracted with AcOEt. The extracts were combined, filtered, washed with water and dried over sodium sulphate. The solvent was removed in vacuo. The residue was chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%, then MeOH/CH2Cl2 from 0 to 7%) to give the desired 2-(4-ethyl-phenyl)-8-[2-(2-oxo-pyrrolidin-1-yl)-benzenesulfonyl]-2,8-diaza-spiro[4.5]decan-1-one as a yellow oil. MS (ESI): 482.21 (MH+).

Workup

  1. extractionextracted with AcOEt
  2. filtrationfiltered
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was removed in vacuo
  6. customThe residue was chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%

Sources & evidence

ORD record
ord-ee34bdda7a1542cd8948d6b4013ce93a
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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