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Sodium Iodide → N-(1-{2-[3-(2,6-Dimethyl-pyridin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-N-ethyl-4-methoxy-benzenesulfonamide

HRID 2354076
Notes
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Reaction equation

HRID 2354076 reaction equation
[CH2:1]([N:3]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[S:4]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].C([O-])(O)=O.[Na+].[Na+].[I-].Cl[CH2:29][CH2:30][NH:31][C:32]([NH:34][C:35]1[CH:40]=[C:39]([CH3:41])[N:38]=[C:37]([CH3:42])[CH:36]=1)=[O:33]>C1COCC1>[CH3:41][C:39]1[CH:40]=[C:35]([NH:34][C:32](=[O:33])[NH:31][CH2:30][CH2:29][N:18]2[CH2:19][CH2:20][CH:15]([N:3]([CH2:1][CH3:2])[S:4]([C:7]3[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=3)(=[O:5])=[O:6])[CH2:16][CH2:17]2)[CH:36]=[C:37]([CH3:42])[N:38]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 588165671-(2-Chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-ureaHCID 58816568N-Ethyl-4-methoxy-N-piperidin-4-yl-benzenesulfonamide

Product 1

HCID 11294764N-(1-{2-[3-(2,6-Dimethyl-pyridin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-N-ethyl-4-methoxy-benzenesulfonamide

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of N-ethyl-4-methoxy-N-piperidin-4-yl-benzenesulfonamide (Example A4., 2.09 g, 7.0 mmol), NaHCO3 (3.4 g, 40 mmol), NaI (0.75 g, 5 mmol) and 1-(2-chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-urea (Example D1, 1.14 g 5 mmol) in THF (30 mL) is stirred at 50° C. for 27 days. The mixture is quenched with Na2CO3 (150 mL) and extracted with CH2Cl2 (3×100 mL). The organic extracts are washed with sat. aq. Na2CO3 (70 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by MPLC to provide the title compound.

Workup

  1. customThe mixture is quenched with Na2CO3 (150 mL)
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. washThe organic extracts are washed with sat. aq. Na2CO3 (70 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by MPLC

Sources & evidence

ORD record
ord-1b4808b58ec74821946649715966a947
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07750161B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes