N,N-Diethylethylenediamine → HCID 9893615、化合物

HRID 411776

反応式

HRID 411776 の反応式
[OH:1][CH2:2][N:3]1[C:7](=[O:8])[C:6]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[C:5]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH3:31])[CH:23]=2)[C:4]1=[O:32].[N+](C1C=C[C:39]([O:42]C(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.[CH2:55]([N:57]([CH2:60][CH2:61][NH2:62])[CH2:58]C)C>C1COCC1>[CH3:31][N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:5]2[C:4](=[O:32])[N:3]([CH2:2][O:1][C:39](=[O:42])[NH:62][CH2:61][CH2:60][N:57]([CH3:58])[CH3:55])[C:7](=[O:8])[C:6]=2[C:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:21])[CH:10]=2)=[CH:23]1

参加物

5

反応物 3

HCID 60993N,N-DiethylethylenediamineHCID 78756Bis(4-nitrophenyl) carbonateHCID 98673381-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

生成物 1

HCID 9893615HCID 9893615、化合物収率 48.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

1-Hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (200 mg, 0.47 mmol), prepared as in example 1a, was dissolved in THF (10 mL). The resulting red solution was cooled in an ice bath. Lithium bis(trimethylsiliyl)amide (0.56 mL, 0.56 mmol, 1 M in THF) was added dropwise to the solution to give a red suspension. After 10 min, bis(p-nitrophenyl)carbonate (200 mg, 0.66 mmol) was added. The resulting solution was stirred at 0° C. for 20 min. Diethylaminoethylamine (90 mg, 0.78 mmol) in THF (2 mL) was added. Stirring was continued for 2 hrs. The mixture was evaporated and the residue was purified by flash chromatography to give (2-dimethylamino-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (124 mg 46%).

後処理

  1. temperatureThe resulting red solution was cooled in an ice bath
  2. customto give a red suspension
  3. stirringStirring
  4. waitwas continued for 2 hrs
  5. customThe mixture was evaporated
  6. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-1d1ee7fff9e34af1a5d27df8ceb736b7
出典データセット
uspto-grants-2003_05
特許番号
US06559164B1

関連ノート

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