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 61779Notes

Reaction equation

HRID 61779 reaction equation
[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

Participants

6

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-5d11cb63d7f740bc83a811bed9a4ccf2
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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