Sodium Bicarbonate → 9-Amino-6,6-dimethyl-8-(1-methyl-piperidin-4-yl oxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61779ノート

反応式

HRID 61779 の反応式
[CH3:1][C:2]1([CH3:33])[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:15]#[N:16])[CH:11]=3)[C:6]=2[C:5](=[O:17])[C:4]2[CH:18]=[C:19]([N+:30]([O-])=O)[C:20]([O:22][CH:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)=[CH:21][C:3]1=2.C([O-])(=O)C.[NH4+].C(=O)([O-])O.[Na+]>C(O)C.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:30][C:19]1[C:20]([O:22][CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:21][C:3]2[C:2]([CH3:33])([CH3:1])[C:14]3[NH:13][C:12]4[C:7]([C:6]=3[C:5](=[O:17])[C:4]=2[CH:18]=1)=[CH:8][CH:9]=[C:10]([C:15]#[N:16])[CH:11]=4

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 668344326,6-Dimethyl-8-(1-methyl-piperidin-4-yloxy)-9-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile2 回

生成物 1

HCID 668343889-Amino-6,6-dimethyl-8-(1-methyl-piperidin-4-yl oxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile収率 78%

試薬・触媒・溶媒 2

HCID 10313229titanium(III) trichloride触媒HCID 702Ethanol溶媒

実験手順

6,6-Dimethyl-8-(1-methyl-piperidin-4-yl oxy)-9-nitro-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound D1, 83 mg, 0.19 mmol) was dissolved in ethanol, added with aqueous solution of ammonium acetate and aqueous solution of titanium (III) chloride, and then the mixture was stirred at room temperature for 45 min. The reaction solution was added to saturated aqueous solution of sodium hydrogen carbonate and then 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 were concentrated under reduced pressure to obtain the title compound (yellow solid, 60 mg, 78%).

後処理

  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. concentrationthe residues were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-5d11cb63d7f740bc83a811bed9a4ccf2
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

反応ノート

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