Sodium Iodide → 1-[2-(1-Adamantyl)ethyl]-1-[2-[N-(2-methoxyethyl)-N-methylamino]ethyl]-3-[3-(4-pyridyl)propyl]urea

HRID 18408

Reaction equation

HRID 18408 reaction equation
[C:1]12([CH2:11][CH2:12][N:13]([CH2:26][CH2:27][NH:28][CH3:29])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:38][O:39][CH2:40][CH2:41]Cl>O.C(OCC)C.CN(C)C=O>[C:1]12([CH2:11][CH2:12][N:13]([CH2:26][CH2:27][N:28]([CH2:41][CH2:40][O:39][CH3:38])[CH3:29])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 121366481-[2-(1-Adamantyl)ethyl]-1-(2-methylaminoethyl)-3-[3-(4-pyridyl)propyl]urea

Product 1

HCID 121366521-[2-(1-Adamantyl)ethyl]-1-[2-[N-(2-methoxyethyl)-N-methylamino]ethyl]-3-[3-(4-pyridyl)propyl]ureaYield 32.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To N,N-dimethylformamide (20 ml) were added 1-[2-(1-adamantyl)ethyl]-1-(2-methylaminoethyl)-3-[3-(4-pyridyl)propyl]urea (1.50 g, 3.76 mmol), which is a free base of Compound No. 3-1, potassium carbonate (1.56 g, 11.3 mmol) and sodium iodide (1.69 g, 11.3 mmol) at room temperature, then 2-chloroethyl methyl ether (412 μl, 4.51 mmol) was added to the mixture, and the whole was heated at 80° C. and stirred overnight, then diethyl ether (50 ml) and water (100 ml) were added to the reaction mixture. After extraction, the obtained organic layer was washed with water (100 ml) and a saturated aqueous sodium chloride solution (50 ml) successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the target compound (552 mg, 32.1%) as a pale yellow oily matter.

Workup

  1. extractionAfter extraction
  2. washthe obtained organic layer was washed with water (100 ml)
  3. dry with materiala saturated aqueous sodium chloride solution (50 ml) successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3546c6bb4a4d4bae84b243bf1d9b5bef
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Linked notes

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