ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylate → ethyl 1-(4-{[1-methyl-3-({[(1-methylethyl)oxy]carbonyl}amino)-3-oxopropyl]amino}phenyl)-1H-imidazole-4-carboxylate

HRID 2366878

반응식

HRID 2366878 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[C:18]([NH:23][C:24](=[O:29])[O:25][CH:26]([CH3:28])[CH3:27])(=[O:22])/[CH:19]=[CH:20]/[CH3:21]>C(#N)C.O.O.O.O.O.O.[N+]([O-])([O-])=O.[Y+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[CH3:21][CH:20]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[CH:9]2)=[CH:6][CH:7]=1)[CH2:19][C:18]([NH:23][C:24]([O:25][CH:26]([CH3:27])[CH3:28])=[O:29])=[O:22]

참가 물질

5

반응물 2

HCID 18726772ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylateHCID 866691361-methylethyl (2E)-2-butenoylcarbamate2회

생성물 1

HCID 67208063ethyl 1-(4-{[1-methyl-3-({[(1-methylethyl)oxy]carbonyl}amino)-3-oxopropyl]amino}phenyl)-1H-imidazole-4-carboxylate수율 31%

시약·촉매·용매 2

HCID 166833Yttrium (III) nitrate hexahydrate (1:3:6)촉매HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of ethyl 1-(4-aminophenyl)-1H-imidazole-4-carboxylate (for a preparation see intermediate 85) (9.4 g, 40.6 mmol), 1-methylethyl (2E)-2-butenoylcarbamate (for a preparation see intermediate 49) (6.96 g, 40.6 mmol), and yttrium nitrate hexahydrate (1.56 g, 4.06 mmol) in dry acetonitrile (200 mL) was stirred at 60° C. for 48 h then cooled to room temperature and concentrated in vacuo. The residue was suspended in AcOEt (250 mL) and the organic phase was washed with water (×2) then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 60-100% AcOEt in Hexanes followed by 0 to 5% methanol in AcOEt) gave ethyl 1-(4-{[1-methyl-3-({[(1-methylethyl)oxy]carbonyl}amino)-3-oxopropyl]amino}phenyl)-1H-imidazole-4-carboxylate (5 g, 12.42 mmol, 31%) as a colourless gum.

후처리

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. washthe organic phase was washed with water (×2)
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (gradient: 60-100% AcOEt in Hexanes followed by 0 to 5% methanol in AcOEt)

출처 및 근거

ORD 기록
ord-444e82ec73fd487c8121314434b8277b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697725B2

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