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Ethylenediamine → 1-Benzyl-N-(3,4-difluorobenzyl)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-isopropyl-1H-indole-3-carboxamide

HRID 40078
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HRID 40078 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=O)[CH:15]=2)[C:10]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[O:20])=[C:9]1[CH:31]([CH3:33])[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34]([NH2:37])[CH2:35][NH2:36].C1C(=O)N(Br)C(=O)C1>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[NH:36][CH2:35][CH2:34][N:37]=3)[CH:15]=2)[C:10]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=2)=[O:20])=[C:9]1[CH:31]([CH3:32])[CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 3301EthylenediamineHCID 67184N-bromobutanimideHCID 597623731-Benzyl-N-(3,4-difluorobenzyl)-6-formyl-2-isopropyl-1H-indole-3-carboxamide2회

생성물 1

HCID 597622791-Benzyl-N-(3,4-difluorobenzyl)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-isopropyl-1H-indole-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 1-benzyl-N-(3,4-difluorobenzyl)-6-formyl-2-isopropyl-1H-indole-3-carboxamide (Compound 53, 18 mg, 0.040 mmol) in CH2Cl2 (1 ml) at 0° C. under argon was added ethylene diamine (2.5 mg, 0.042 mmol). The mixture was stirred at 0° C. for 30 minutes, and then added NBS (8 mg, 0.042 mmol). The reaction was stirred at 25° C. for 12 h, quenched with NaHCO3 (aqueous), diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified by chromatography on silica gel (100% EtOAc) to yield the title compound as a light yellow solid.

후처리

  1. stirringThe reaction was stirred at 25° C. for 12 h
  2. customquenched with NaHCO3 (aqueous)
  3. additiondiluted with EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (100% EtOAc)

출처 및 근거

ORD 기록
ord-7ed5fff473e34b04b84139b4dcfc2216
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524917B2

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