Isonicotinic Acid → isonicotinic 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

HRID 411769

反応式

HRID 411769 の反応式
CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C.[N:22]1[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][CH:23]=1.O[CH2:32][N:33]1[C:37](=[O:38])[C:36]([C:39]2[C:47]3[C:42](=[CH:43][C:44]([N+:48]([O-:50])=[O:49])=[CH:45][CH:46]=3)[N:41]([CH3:51])[CH:40]=2)=[C:35]([C:52]2[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[N:54]([CH3:61])[CH:53]=2)[C:34]1=[O:62]>C(Cl)Cl>[CH3:61][N:54]1[C:55]2[C:60](=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:52]([C:35]2[C:34](=[O:62])[N:33]([CH2:32][O:29][C:28](=[O:30])[C:25]3[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=3)[C:37](=[O:38])[C:36]=2[C:39]2[C:47]3[C:42](=[CH:43][C:44]([N+:48]([O-:50])=[O:49])=[CH:45][CH:46]=3)[N:41]([CH3:51])[CH:40]=2)=[CH:53]1

参加物

6

反応物 4

HCID 5922Isonicotinic AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 9871825isonicotinic 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収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of dimethylaminopyridine (1.5 equivalents) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.5 equivalent) in CH2Cl2 was added 4-picolinic acid (1.2 equivalents) and the reaction mixture was stirred a few minutes. 1-Hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione, prepared as in example 1a, was added and the reaction mixture was stirred at room temperature for several hours. The mixture was diluted with dichloromethane, washed with aqueous HCL, saturated NaHCO3, water, dried over MgSO4 and evaporated. The residue was purified by column chromatography to afford isonicotinic 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 (yield—76%).

後処理

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for several hours
  3. washwashed with aqueous HCL, saturated NaHCO3, water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-69835ae76d5144569ca28fdf7721c8a5
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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