Ethyl isocyanate → 1-Ethyl-3-(2-(4-(6-methoxy-napthalen-2-yl)-5-pyridin-4-yl-1H-imidazol-2-yl)-2-methyl-propyl)-urea

HRID 457898Notes

Reaction equation

HRID 457898 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[N:14]=[C:15]([C:24]([CH3:28])([CH3:27])[CH2:25][NH2:26])[NH:16][C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH:7]=[CH:6]2.CCN(C(C)C)C(C)C.[CH2:38]([N:40]=[C:41]=[O:42])[CH3:39]>ClCCl.O>[CH2:38]([NH:40][C:41]([NH:26][CH2:25][C:24]([C:15]1[NH:16][C:17]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)[N:14]=1)([CH3:28])[CH3:27])=[O:42])[CH3:39]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 18440775HCID 18440775, compound

Product 1

HCID 184407621-Ethyl-3-(2-(4-(6-methoxy-napthalen-2-yl)-5-pyridin-4-yl-1H-imidazol-2-yl)-2-methyl-propyl)-ureaYield 54.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 2 (20 mg, 0.05 mmol) in dichloromethane (2 mL) containing Hunig's base (10 μL, 0.07 mmol) was treated with ethyl isocyanate (6 μL, 0.07 mmol) and stirred at room temperature for 8 hours. The mixture was diluted with water and extracted with dichloromethane. The aqueous layer was separated and extracted with additional dichloromethane, the organic layers were combined, dried over anhydrous magnesium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on a Gilson HPLC to give the title compound (12 mg, 50%) as a yellow solid; MS(ES) m/e 444 [M+H]+.

Workup

  1. extractionextracted with dichloromethane
  2. customThe aqueous layer was separated
  3. extractionextracted with additional dichloromethane
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on a Gilson HPLC

Sources & evidence

ORD record
ord-f0af50b8c03e4a75aec4230191cf4edd
Source dataset
uspto-grants-2007_03
Patent number
US07189745B1

Reaction notes

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