Sodium Iodide → (1-{2-[3-(2,6-Dimethyl-pyridin-4-yl)-ureido]-ethyl}-piperidin-4-yl)-methyl-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:15])[N:7]([CH3:14])[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[Na+].[I-].Cl[CH2:24][CH2:25][NH:26][C:27]([NH:29][C:30]1[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([CH3:37])[CH:31]=1)=[O:28]>C1COCC1>[C:1]([O:5][C:6](=[O:15])[N:7]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:24][CH2:25][NH:26][C:27]([NH:29][C:30]2[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([CH3:37])[CH:31]=2)=[O:28])[CH2:10][CH2:9]1)[CH3:14])([CH3:4])([CH3:3])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A suspension of methyl-piperidin-4-yl-carbamic acid tert-butyl ester (3.57 g, 16.7 mmol), NaHCO3 (6.7 g, 79 mmol), NaI (1.5 g, 10 mmol) and 1-(2-chloro-ethyl)-3-(2,6-dimethyl-pyridin-4-yl)-urea (Example D1, 2.14 g 9.4 mmol) in THF (30 mL) is stirred at 50° C. for 14 days. The mixture is quenched with Na2CO3 (50 mL) and extracted with CH2Cl2 (5×50 mL). The organic extracts are washed with sat. aq. Na2CO3 (30 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by FC to provide the title compound.
Workup
- customThe mixture is quenched with Na2CO3 (50 mL)
- extractionextracted with CH2Cl2 (5×50 mL)
- washThe organic extracts are washed with sat. aq. Na2CO3 (30 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe residue is purified by FC
Sources & evidence
- ORD record
- ord-1b496d75bbb24013afbe7cf37c2bc6be
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750161B2
Reaction notes
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