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 61779노트

반응식

HRID 61779 반응식
[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

참가 물질

6

반응물 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-carbonitrile2회

생성물 1

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

시약·촉매·용매 2

HCID 10313229titanium(III) trichloride촉매HCID 702Ethanol용매

실험 절차

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%).

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. concentrationthe residues were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5d11cb63d7f740bc83a811bed9a4ccf2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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