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1H-Indole-7-carboxylic acid → 1H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide

HRID 855248
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반응식

HRID 855248 반응식
CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:22]([OH:24])=O)[CH:15]=[CH:14]1.[C:25]([C:29]1[CH:30]=[CH:31][C:32]([CH2:36][NH:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[C:33]([OH:35])[CH:34]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([CH2:36][N:37]([CH2:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)[C:22]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:21]=2[NH:13][CH:14]=[CH:15]3)=[O:24])=[C:33]([OH:35])[CH:34]=1)([CH3:28])([CH3:26])[CH3:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 742811H-Indole-7-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 693423465-Tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol

생성물 1

HCID 866030371H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide수율 82%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

1.69 g (8.8 mmol) of EDC.HCl were added to 1.46 g (8.8 mmol) of 1H-indol-7-carboxylic acid and 2.41 g (8.8 mmol) of 5-tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol dissolved in 80 ml DCM. The reaction mixture was stirred at rt over night, diluted with DCM and washed once with water and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (250 g silica gel; heptane/EtOAc 7:3) to yield 2.9 g (82%) 1H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide as a colorless foam. MS (ISP) 445.3 (M+H)+.

후처리

  1. washwashed once with water and once with saturated aqueous NaCl solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography (250 g silica gel; heptane/EtOAc 7:3)

출처 및 근거

ORD 기록
ord-64323683dbaa4314b418e0680cb74bff
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07259183B2

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