3-Ethylphenyl isocyanate → 2-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

HRID 530425

반응식

HRID 530425 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:17]([NH2:19])=[O:18])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[CH2:20]([C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]>C1COCC1.C(OCC)(=O)C>[CH2:20]([C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]([C:17]([NH2:19])=[O:18])[C:10]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:4][CH:3]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)[CH3:21]

참가 물질

5

반응물 2

HCID 27696373-Ethylphenyl isocyanateHCID 1212546212-(4-Amino-phenyl)-indole-1-carboxylic acid amide

생성물 1

HCID 1212546082-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

The reaction mixture of 2-(4-amino-phenyl)-indole-1-carboxylic acid amide (125.5 mg, 0.5 mmol, 1 eq) and 3-ethylphenyl isocyanate (0.073 mL, 1 eq) in anhydrous THF (4 mL) was stirred at room temperature for 2 hours. It was then diluted with ethyl acetate, washed sequentially with aqueous NH4Cl, saturated aqueous NaHCO3, brine, and dried with anhydrous sodium sulfate. The upper liquor was decanted, concentrated, and the solid residue was triturated with EtOAC-Hex (1:1). 2-[4-({[(3-ethylphenyl)amino]carbonyl}amino)phenyl]-1H-indole-1-carboxamide was obtained as white solid upon filtration in amount of 156 mg (78%).

후처리

  1. washwashed sequentially with aqueous NH4Cl, saturated aqueous NaHCO3, brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper liquor was decanted
  4. concentrationconcentrated
  5. customthe solid residue was triturated with EtOAC-Hex (1:1)

출처 및 근거

ORD 기록
ord-de42bfbb51354e47b5692def9fbaddc0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353093B2

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