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

HRID 1458361노트

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HRID 1458361 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b704dd34c9244217b3aa48bd653ab527
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849764

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