Sodium Iodide → 2-(4-Chloro-phenyl)-N-(1-{2-[3-(2,6-dimethyl-pyridin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-N-ethyl-acetamide

HRID 2354075Notes

Reaction equation

HRID 2354075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH2:18][CH3:19])[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[Na+].[I-].Cl[CH2:28][CH2:29][NH:30][C:31]([NH:33][C:34]1[CH:39]=[C:38]([CH3:40])[N:37]=[C:36]([CH3:41])[CH:35]=1)=[O:32]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:28][CH2:29][NH:30][C:31]([NH:33][C:34]3[CH:39]=[C:38]([CH3:40])[N:37]=[C:36]([CH3:41])[CH:35]=3)=[O:32])[CH2:14][CH2:13]2)[CH2:18][CH3:19])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 588165671-(2-Chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-ureaHCID 608067452-(4-chloro-phenyl)-N-ethyl-N-piperidin-4-yl-acetamide

Product 1

HCID 112252192-(4-Chloro-phenyl)-N-(1-{2-[3-(2,6-dimethyl-pyridin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-N-ethyl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-(4-chloro-phenyl)-N-ethyl-N-piperidin-4-yl-acetamide (Example A10., 3.37 g, 12.0 mmol), NaHCO3 (5.4 g, 64 mmol), NaI (1.2 g, 8 mmol) and 1-(2-chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-urea (Example D1, 1.82 g 8 mmol) in THF (40 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-50a5473ba79f47798c034fa9850058f4
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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