Trifluoroacetic acid → 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide

HRID 1458361ノート

反応式

HRID 1458361 の反応式
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19](=[O:29])[N:20]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]=2)[NH:12][C:11]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:21]([N:20]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:30]1[CH:31]=[C:32]([CH3:37])[CH:33]=[C:34]([CH3:36])[CH:35]=1)=[C:10]2[CH2:9][CH2:8][NH2:7])=[O:29])[CH:22]([CH3:24])[CH3:23]

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 54298340{2-[5-diisobutylcarbamoyl-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}carbamic acid tert-butyl ester

生成物 1

HCID 537946513-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide収率 93.2%

反応条件

温度
0 °C

実験手順

To a solution of {2-[5-diisobutylcarbamoyl-2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-ethyl}carbamic acid tert-butyl ester (230 mg in 12 mL methylene chloride) at 0° C. was added 0.55 mL anisole followed by 3.4 mL trifluoroacetic acid and the mixture stirred at 0° C. After 1 hour, the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1) gave the title compound (173 mg).

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residual acid removed by azeotrope with toluene
  3. customPurification of the
  4. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1)

出典と根拠

ORDレコード
ord-b704dd34c9244217b3aa48bd653ab527
出典データセット
uspto-grants-1998_12
特許番号
US05849764

反応ノート

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