1,1'-Carbonyldiimidazole → N-(5-(tert-butyl)-2-(2,5-dimethylpyrrolyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea

HRID 491094

반응식

HRID 491094 반응식
[CH:1]1N=C[N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[C:13]([C:17]1[CH:18]=[CH:19][C:20]([C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][C:25]=2[CH3:30])=C(C=1)N)([CH3:16])([CH3:15])[CH3:14].[CH3:31][NH:32][C:33]([C:35]1[CH:40]=[C:39]([O:41][C:42]2[CH:48]=CC(N)=[CH:44][CH:43]=2)[CH:38]=[CH:37][N:36]=1)=[O:34]>C(Cl)Cl.CCOC(C)=O>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][C:25]=2[CH3:30])=[C:9]([NH:8][C:6]([NH:3][C:2]2[CH:1]=[CH:48][C:42]([O:41][C:39]3[CH:38]=[CH:37][N:36]=[C:35]([C:33](=[O:34])[NH:32][CH3:31])[CH:40]=3)=[CH:43][CH:44]=2)=[O:7])[CH:10]=1)([CH3:14])([CH3:15])[CH3:16]

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 166551294-(4-Aminophenoxy)-N-methylpicolinamideHCID 540501305-Tert-butyl-2-(2,5-dimethylpyrrolyl)aniline

생성물 1

HCID 54135293N-(5-(tert-butyl)-2-(2,5-dimethylpyrrolyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea수율 24.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
36 °C

실험 절차

To a stirring solution of CDI (0.21 g, 1.30 mmol) in CH2Cl2 (2 mL) was added 5-(tert-butyl)-2-(2,5-dimethylpyrrolyl)aniline (Method A4, Step 2; 0.30 g, 1.24 mmol) in one portion. The resulting mixture was stirred at room temp. for 4 h, then 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (0.065 g, 0.267 mmol) was then added in one portion. The resulting mixture was heated at 36° C. overnight, then cooled to room temp. and diluted with EtOAc (5 mL). The resulting mixture was sequentially washed with water (15 mL) and a 1N HCl solution (15 mL), dried (MgSO4), and filtered through a pad of silica gel (50 g) to afford N-(5-(tert-butyl)-2-(2,5-dimethylpyrrolyl)phenyl)-N′-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea as a yellowish solid (0.033 g, 24%): TLC (40% EtOAc/60% hexane) Rf0.24; 1H NMR (acetone-d6) δ 1.37 (s, 9H), 1.89 (s, 6H), 2.89 (d, J=4.8 Hz, 3H), 5.83 (s, 2H), 6.87-7.20 (m, 6H), 7.17 (dd, 1H), 7.51-7.58 (m, 3H), 8.43 (d, J=5.4 Hz, 1H), 8.57 (d, J=2.1 Hz, 1H), 8.80 (brs, 1H); HPLC ES-MS 512 ((M+H)+, 100%).

후처리

  1. temperaturecooled to room temp.
  2. washThe resulting mixture was sequentially washed with water (15 mL)
  3. dry with materiala 1N HCl solution (15 mL), dried (MgSO4)
  4. filtrationfiltered through a pad of silica gel (50 g)

출처 및 근거

ORD 기록
ord-6b6c9a4dcd5d49868b1ee3ac97dff3a8
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528255B2

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