Sodium Iodide → 1-{2-[4-(2-Methoxy-phenyl)-piperidin-1-yl]-ethyl}3-(2-methyl-quinolin-4-yl)-urea

HRID 2223705Notes

Reaction equation

HRID 2223705 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Cl[CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1)=[O:20].[C:32]([O-])(O)=O.[Na+].[Na+].[I-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([CH3:32])[CH:23]=2)=[O:20])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 5447384-(2-Methoxyphenyl)piperidineHCID 226433981-(2-Chloroethyl)-3-quinolin-4-yl-urea

Product 1

HCID 597159221-{2-[4-(2-Methoxy-phenyl)-piperidin-1-yl]-ethyl}3-(2-methyl-quinolin-4-yl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(2-methoxy-phenyl)-piperidine (0.03 mmol) in dry THF (1 mL) is added 1-(2-chloro-ethyl)-3-quinolin-4-yl-urea (0.03 mmol), solid NaHCO3 (2.5 mg), and NaI (1 mg). The flask is tightly sealed, and shaken at 70° C. for 6 days. The reaction mixture is evaporated, taken up in aqueous formic acid, and purified by preparative HPLC to provide the title compound.

Workup

  1. customThe flask is tightly sealed
  2. customThe reaction mixture is evaporated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c0ea3cda6dd04733a0615f3984c9d838
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

Loading…