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

HRID 2354076Notes

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

Participants

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

customThe mixture is quenched with Na2CO3 (150 mL)
extractionextracted with CH2Cl2 (3×100 mL)
washThe organic extracts are washed with sat. aq. Na2CO3 (70 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated
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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