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 457898노트

반응식

HRID 457898 반응식
[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]

참가 물질

6

반응물 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 18440775HCID 18440775, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-f0af50b8c03e4a75aec4230191cf4edd
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189745B1

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