N,N-Diethylethylenediamine → 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrole-1-carboxylic acid (2-diethylamino-ethyl)-amide

HRID 411779

반응식

HRID 411779 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:30])[NH:13][C:14](=[O:29])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=3)[N:18]([CH3:28])[CH:17]=2)=[CH:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N+](C1C=C[C:47]([O:50]C(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.[CH2:63]([N:65]([CH2:68][CH2:69][NH2:70])[CH2:66][CH3:67])[CH3:64]>C1COCC1>[CH2:63]([N:65]([CH2:66][CH3:67])[CH2:68][CH2:69][NH:70][C:47]([N:13]1[C:14](=[O:29])[C:15]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=3)[N:18]([CH3:28])[CH:17]=2)=[C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)[C:12]1=[O:30])=[O:50])[CH3:64]

참가 물질

6

반응물 4

HCID 60993N,N-DiethylethylenediamineHCID 78756Bis(4-nitrophenyl) carbonateHCID 2733832Lithium HexamethyldisilazideHCID 53276861H-pyrrole-2,5-dione, 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-

생성물 1

HCID 98503203-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrole-1-carboxylic acid (2-diethylamino-ethyl)-amide수율 10.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a cold solution of 3-(1-Methyl-3-indolyl)-4-(1-methyl-6-nitro-3-indolyl)-1H-pyrrole-2,5-dione (200 mg, 0.5 mmol) (see Davis U.S. Pat. No. 5,057,614) in THF (7 mL) was added dropwise, lithium bis(trimethylsilyl)amide (0.55 mmol, 0.55 mL, 1 M in THF). The resulting red suspension was stirred for 15 min. Bis(p-nitrophenyl)carbonate (213 mg, 0.7 mmol) was added. The solution was stirred at 0° C. for 0.5 h. Diethylaminoethylamine (69.7 mg, 0.6 mmol) in THF (2 mL) was added, and stirring was continued for 2 h. The solvent was evaporated and the residue was purified by flash chromatography to give 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrole-1-carboxylic acid (2-diethylamino-ethyl)-amide (28 mg, 10%).

후처리

  1. stirringThe solution was stirred at 0° C. for 0.5 h
  2. stirringstirring
  3. waitwas continued for 2 h
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-d53d946c859d400989ebf0858bba6426
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559164B1

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