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Triethylamine → N-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-phenyl]-2-methylsulfanyl-benzamide

HRID 439957
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HRID 439957 반응식
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].C(N(CC)CC)C.[NH2:19][C:20]1[CH:41]=[CH:40][C:23]([C:24]([N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][N:29]3[CH:37]=[CH:38][CH:39]=[C:28]3[CH2:27]2)=[O:25])=[CH:22][CH:21]=1>C(Cl)Cl>[CH:39]1[CH:38]=[CH:37][N:29]2[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N:26]([C:24]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:5](=[O:6])[C:4]4[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=4[S:2][CH3:1])=[CH:41][CH:40]=3)=[O:25])[CH2:27][C:28]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 125767982-(Methylsulfanyl)benzoyl chloride

생성물 1

HCID 21837162N-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-phenyl]-2-methylsulfanyl-benzamide수율 54.3%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

To a stirred solution of 0.364 g of 2-(methylthio)benzoyl chloride 5 ml of methylene chloride is added 0.346 g of triethylamine at 0° C. After stirring for 3 minutes, 0,500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added and stirring continued for 72 hours at room temperature. The reaction mixture is diluted with 45 ml of methylene chloride and washed with water, 2N citric acid, NaHCO 3, and brine. The reaction mixture is dried with N2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography using 1:1 ethyl acetate-hexane to give a solid which is crystallized from ethyl alcohol to give 0.480 g of the desired product as a white solid, m.p. 71°-174° C.

후처리

  1. stirringstirring
  2. waitcontinued for 72 hours at room temperature
  3. washwashed with water, 2N citric acid, NaHCO 3, and brine
  4. customThe reaction mixture is dried with N2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a solid which
  8. customis purified by flash chromatography
  9. customto give a solid which
  10. customis crystallized from ethyl alcohol

출처 및 근거

ORD 기록
ord-633e2354c8234581b8725ee487e6d84e
출처 데이터셋
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05516774

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