Tetrahydrofuran → 9-Acetyl-8-[4-(1,1-dimethyl-prop-2-ynyl)-piperazin-1-yl]-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61796

反応式

HRID 61796 の反応式
C1COCC1.[C:6]([C:9]1[C:30]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:29][C:12]2[C:13]([CH3:28])([CH3:27])[C:14]3[NH:15][C:16]4[C:21]([C:22]=3[C:23](=[O:24])[C:11]=2[CH:10]=1)=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=4)(=[O:8])[CH3:7].Cl[C:38]([CH3:42])([CH3:41])[C:39]#[CH:40].C(N(CC)CC)C>[Cu]Cl.O>[C:6]([C:9]1[C:30]([N:31]2[CH2:32][CH2:33][N:34]([C:38]([CH3:42])([CH3:41])[C:39]#[CH:40])[CH2:35][CH2:36]2)=[CH:29][C:12]2[C:13]([CH3:28])([CH3:27])[C:14]3[NH:15][C:16]4[C:21]([C:22]=3[C:23](=[O:24])[C:11]=2[CH:10]=1)=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=4)(=[O:8])[CH3:7]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 706791-Butyne, 3-chloro-3-methyl-HCID 668342259-acetyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

生成物 1

HCID 866638229-Acetyl-8-[4-(1,1-dimethyl-prop-2-ynyl)-piperazin-1-yl]-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile収率 35%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 962Water溶媒

実験手順

To the anhydrous THF solution (0.5 mL) of 9-acetyl-6,6-dimethyl-11-oxo-8-piperazin-1-yl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound H8-5, 25 mg, 0.06 mmol), 3-chloro-3-methyl-but-1-yne (0.013 mL, 0.12 mmol), copper (I) chloride (0.6 mg, 0.006 mmol) and triethylamine (0.017 mL, 0.12 mmol) were added at room temperature. After stirring for 30 min, the mixture was added with water and extracted with ethyl acetate. The organic layer was dried over magnesium 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 (dichloromethane/methanol) to obtain the title compound (white solid, 9.8 mg, 35%).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by amino silica gel column chromatography (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-bd5b2995ffff48a3b42d46972faac34f
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

関連ノート

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