Potassium Carbonate → HCID 49806722、化合物

HRID 2202443

反応式

HRID 2202443 の反応式
Br[C:2]1[C:23]([N:24]2[CH2:29]CN(C3CCC3)[CH2:26][CH2:25]2)=[CH:22][C:5]2C(C)(C)C3NC4C(C=3C(=O)C=2C=1)=CC=C(C#N)C=4.CB1OB(C)OB(C)O1.[C:43](=[O:46])([O-])[O-].[K+].[K+].C1(N2CC[N:56]([C:59]3[C:60]([CH3:81])=[CH:61][C:62]4[C:74](=[O:75])[C:73]5[C:72]6[C:67](=[CH:68][C:69]([C:76]#[N:77])=[CH:70][CH:71]=6)[NH:66][C:65]=5[C:64]([CH3:79])([CH3:78])[C:63]=4[CH:80]=3)[CH2:55]C2)CCC1>CN(C)C=O>[CH3:78][C:64]1([CH3:79])[C:65]2[NH:66][C:67]3[C:72](=[CH:71][CH:70]=[C:69]([C:76]#[N:77])[CH:68]=3)[C:73]=2[C:74](=[O:75])[C:62]2[CH:61]=[C:60]([CH3:81])[C:59]([N:56]3[CH2:55][CH2:2][CH:23]([N:24]4[CH2:29][CH2:43][O:46][CH2:26][CH2:25]4)[CH2:22][CH2:5]3)=[CH:80][C:63]1=2

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 498048699-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 668347598-(4-Cyclobutyl-piperazin-1-yl)-6,6,9-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

生成物 1

HCID 49806722HCID 49806722、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

With the same condition as the method for synthesizing the Compound F5-47 (under nitrogen atmosphere, to the N,N-dimethyl formamide (1.5 ml) solution of 9-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound F4-10, 50 mg, 0.099 mmol), trimethyl boroxine (12 mg, 0.1 eq.), tetrakis triphenylphosphine palladium (39 mg, 0.2 eq.), and potassium carbonate (41 mg, 3.0 eq.) were added, and the mixture was stirred at 100° C. for 24 hours. Upon the completion of the reaction, distilled water was poured into the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with aqueous solution of sodium chloride and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/methanol) to obtain the Compound F5-47 (8-(4-cyclobutyl-piperazin-1-yl)-6,6,9-trimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile) (25 mg, 58%)), the title compound was synthesized from the Compound F3-11.

後処理

  1. customWith the same condition as the method for synthesizing the Compound
  2. customUpon the completion of the reaction
  3. distillationdistilled water
  4. additionwas poured into the reaction solution, which
  5. extractionwas then extracted with ethyl acetate
  6. washThe organic layer was washed with aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customThe drying agent was removed by filtration
  9. customthe residues obtained
  10. concentrationafter concentration under reduced pressure
  11. customwere purified by silica gel column chromatography (ethyl acetate/methanol)
  12. customto obtain the Compound

出典と根拠

ORDレコード
ord-8d278704e17d47fbaa1dbab9a2bafe06
出典データセット
uspto-grants-2016_06
特許番号
US09365514B2

関連ノート

読み込み中…