Pyridine → HCID 22975843, compound

HRID 1860215Notes

Reaction equation

HRID 1860215 reaction equation
[CH:1]1([CH2:6][CH:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[C:8]([NH:10][C:11]([NH2:13])=[O:12])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.C([CH:30]([C:34](Cl)=[O:35])[C:31](Cl)=[O:32])C.[C:37](OCC)(=[O:39])[CH3:38]>C1(C)C=CC=CC=1>[CH2:37]([O:39][C:34](=[O:35])[CH2:30][C:31]([NH:13][C:11]([NH:10][C:8](=[O:9])[CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:12])=[O:32])[CH3:38]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 8857Ethyl AcetateHCID 109209242-Ethylpropanedioyl dichloride2×HCID 18626611HCID 18626611, compound

Product 1

HCID 22975843HCID 22975843, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of [3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-urea (prepared in Example 1B-d, 402 mg, 1.22 mmol) and pyridine (0.15 mL, 1.83 mmol), in toluene (15 mL) was treated with ethyl malonyl chloride (0.19 mL, 1.5 mmol). The resulting reaction mixture was heated at reflux for 2 h. At this time, additional pyridine (0.15 mL, 1.83 mmol) and ethyl malonyl chloride (0.19 mL, 1.5 mmol) were added. The reaction was then heated at reflux for 90 min. The reaction was then cooled to 25° C., diluted with ethyl acetate (50 mL), washed with water (2×25 mL), and dried over magnesium sulfate. The solution was concentrated in vacuo. Flash column chromatography (Merck Silica gel 60, 230-400 mesh, 4/1 hexane/ethyl acetate) afforded 3-{3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-3-oxo-propionic acid ethyl ester (172 mg, 32%) as a colorless gum: EI-HRMS m/e calcd for C20H24Cl2N2O5 (M+) 443.1140, found 443.1128.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 2 h
  4. temperatureThe reaction was then heated
  5. temperatureat reflux for 90 min
  6. washwashed with water (2×25 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2ad336373fa6413eb65dfba8d36593a4
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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