Sodium Bicarbonate → HCID 23152920, compound

HRID 1012272Notes

Reaction equation

HRID 1012272 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:22][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[NH:13][C:12](=O)[CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]1([C:7]2[C:8]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:22][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[NH:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23152739HCID 23152739, compound

Product 1

HCID 23152920HCID 23152920, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 12-cyclohexyl-6-oxo-6,7-dihydro-5H-5,7a,8-triazadibenzo[a,e]azulene-9-carboxylate (111 mg, 0.28 mmol) in tetrahydrofuran (1 ml) was added 1M BH3 THF complex tetrahydrofuran solution (1.6 ml) with stirring under ice-cooling, and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:2) to give ethyl 12-cyclohexyl-6,7-dihydro-5H-5,7a,8-triazadibenzo[a,e]azulene-9-carboxylate (74 mg, yield 69%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-dd8e16f426ff4a1a8f909c56b640c645
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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