Thiophenol → 6-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

HRID 1615026노트

반응식

HRID 1615026 반응식
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH2:22][CH2:23][NH:24]S(C4C=CC=CC=4[N+]([O-])=O)(=O)=O)[C:11]4[CH:12]=[CH:13][C:14]5[C:20](=[O:21])[CH2:19][CH2:18][C:15]=5[C:16]=4[C:17]=3[C:5]=2[CH2:4][CH2:3]1.C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[NH2:24][CH2:23][CH2:22][N:10]1[C:11]2[CH:12]=[CH:13][C:14]3[C:20](=[O:21])[CH2:19][CH2:18][C:15]=3[C:16]=2[C:17]2[C:5]3[CH2:4][CH2:3][C:2](=[O:1])[C:6]=3[CH:7]=[CH:8][C:9]1=2

참가 물질

7

반응물 4

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 71179221N-[2-(3,9-dioxo-1,2,3,9,10,11-hexahydro-6H-dicyclopenta[c,g]carbazol-6-yl)ethyl]-2-nitrobenzenesulfonamide

생성물 1

HCID 453811166-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

Compound 58 (2.2 g, 4.38 mmol) was suspended in a mixture of chloroform (200 mL) and methanol (200 mL). Then Cs2CO3(4.3 g, 13.20 mmol) and at once PhSH (1.3 mL, 12.74 mmol) were added. The solution was refluxed for 18 h (LC/MS monitoring) and evaporated to dryness. Then, an aqueous solution of citric acid was added. The solution obtained was neutralized with an aqueous NaHCO3 solution. The precipitate was filtered off, washed with CH3CN and ether. The product isolated was used in the next step without purification.

후처리

  1. temperatureThe solution was refluxed for 18 h (LC/MS monitoring)
  2. customevaporated to dryness
  3. additionThen, an aqueous solution of citric acid was added
  4. customThe solution obtained
  5. filtrationThe precipitate was filtered off
  6. washwashed with CH3CN and ether
  7. customThe product isolated
  8. customwas used in the next step without purification

출처 및 근거

ORD 기록
ord-60729c3cd6724113993915903b98b1af
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765738B2

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