Tert-Butylamine → 8-(2-Tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2202450

반응식

HRID 2202450 반응식
OC1C=CC2C(=O)C3C4C(=CC(C#N)=CC=4)NC=3C(C)(C)C=2C=1.ClCCN(CC)CC.C(=O)([O-])[O-].[Cs+].[Cs+].C(N(CC)[CH2:41][CH2:42][O:43][C:44]1[CH:45]=[CH:46][C:47]2[C:59](=[O:60])[C:58]3[C:57]4[C:52](=[CH:53][C:54]([C:61]#[N:62])=[CH:55][CH:56]=4)[NH:51][C:50]=3[C:49]([CH3:64])([CH3:63])[C:48]=2[CH:65]=1)C.[C:68]([NH2:72])([CH3:71])([CH3:70])[CH3:69]>CN(C)C(=O)C.O>[C:68]([NH:72][CH2:41][CH2:42][O:43][C:44]1[CH:45]=[CH:46][C:47]2[C:59](=[O:60])[C:58]3[C:57]4[C:52](=[CH:53][C:54]([C:61]#[N:62])=[CH:55][CH:56]=4)[NH:51][C:50]=3[C:49]([CH3:64])([CH3:63])[C:48]=2[CH:65]=1)([CH3:71])([CH3:70])[CH3:69]

참가 물질

8

반응물 5

HCID 6385Tert-ButylamineHCID 10796Cesium carbonateHCID 13364Diethylaminoethyl chlorideHCID 545808678-(2-(diethylamino)ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 668338618-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile2회

생성물 1

HCID 498048718-(2-Tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

반응 조건

온도
100 °C

실험 절차

With the same synthesis condition as the Compound A7-17 (8-hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 25 mg, 0.083 mmol) was dissolved in N,N-dimethylacetamide (1 mL), added with 2-chloroethyldiethylamine (16 mg, 1.1 eq.) and cesium carbonate (54 mg, 2 eq.) in order and stirred at 100° C. for 4 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by amino silica gel column chromatography (ethyl acetate/hexane) to obtain the Compound A7-17 (8-(2-diethylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile) (11 mg, 32%)), the title compound was synthesized from the Compound A7-24 and tert-butyl amine.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by amino silica gel column chromatography (ethyl acetate/hexane)
  8. customto obtain the Compound

출처 및 근거

ORD 기록
ord-9438962a4ed14eb4ae69476d666df3cb
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365514B2

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