5,6,7-Trimethoxy-1H-indole-2-carboxylic acid → HCID 19050056、化合物

HRID 1780222ノート

反応式

HRID 1780222 の反応式
C([O:5][C:6]([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[C:17]([OH:20])[CH:18]=2)[NH:15][C:14]([C:21]([F:24])([F:23])[F:22])=[C:13]3[C:25]([O:27][CH3:28])=[O:26])[CH:10]([CH2:29][Cl:30])[CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl.[CH3:38][O:39][C:40]1[CH:41]=[C:42]2[C:46](=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50])[NH:45][C:44](C(O)=O)=[CH:43]2.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[Cl:30][CH2:29][CH:10]1[C:11]2=[C:12]3[C:16](=[C:17]([OH:20])[CH:18]=[C:19]2[N:8]([C:6]([C:44]2[NH:45][C:46]4[C:42]([CH:43]=2)=[CH:41][C:40]([O:39][CH3:38])=[C:48]([O:49][CH3:50])[C:47]=4[O:51][CH3:52])=[O:5])[CH2:9]1)[NH:15][C:14]([C:21]([F:24])([F:22])[F:23])=[C:13]3[C:25]([O:27][CH3:28])=[O:26]

参加物

7

反応物 4

HCID 8210525,6,7-Trimethoxy-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19050034HCID 19050034、化合物HCID 21866389Hydrogen chloride-ethyl acetate

生成物 1

HCID 19050056HCID 19050056、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To 42.6 mg(95 μmol) of methyl 3-t-butoxycarbonyl-1-chloromethyl-5-hydroxy-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate, 1.6 ml of 3M hydrogen chloride-ethyl acetate was added, and the mixture was stirred at room temperature for one hour. Then the solvent was distilled off. The residue with 23.8 mg (95 mol) of 5,6,7-trimethoxyindole-2-carboxylic acid, and 54.6 mg (285 μmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was stirred in 0.95 ml of anhydrous dimethylformamide at room temperature under atmosphere of argon overnight. Water was added to the liquid reaction mixture. The resulting mixture was extracted with methylene chloride, and the extract solution was washed with water, 10% sodium hydrogencarbonate, and saturated sodium chloride solution successively, and dried over anhydrous sodium sulfate. Therefrom the solvent was distilled off. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain methyl 1-chloromethyl-5-hydroxy-7-trifluoromethyl-3-(5,6,7-trimethoxy-1H-indol-2-ylcarbonyl)-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 45.3 mg (82%).

後処理

  1. distillationThen the solvent was distilled off
  2. extractionThe resulting mixture was extracted with methylene chloride
  3. washthe extract solution was washed with water, 10% sodium hydrogencarbonate, and saturated sodium chloride solution successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationTherefrom the solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-2210770b1822481c8d4cebc3bc8c4f7e
出典データセット
uspto-grants-1997_05
特許番号
US05629430

反応ノート

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