HCID 57815376, compound → HCID 57815343, compound

HRID 1510753Notes

Reaction equation

HRID 1510753 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:33](=[O:34])[CH:32]=[N:31][C:30]5[CH:35]=[CH:36][N:37]=[CH:38][C:29]4=5)[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1>ClCCl.FC(F)(F)C(O)=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH:20]3[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][N:28]4[C:33](=[O:34])[CH:32]=[N:31][C:30]5[CH:35]=[CH:36][N:37]=[CH:38][C:29]4=5)[CH2:24][CH2:25]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57815376HCID 57815376, compound

Product 1

HCID 57815343HCID 57815343, compoundYield 24.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 10 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(3-oxopyrido(3,4-b)pyrazin-4(3H)-yl)ethyl)piperidin-4-yl)carbamate in 1 mL of dichloromethane, 1.0 mL of trifluoroacetic acid was added at room temperature. The mixture was stirred at the same temperature for 4 hours, and the solvent was distilled off under reduced pressure. The resultant residue was charged with chloroform and water and adjusted to pH 0.5 with 1 mol/L hydrochloric acid, and the aqueous layer was separated. Chloroform was added to the aqueous layer, and the aqueous layer was adjusted to pH 12 with a 1 mol/L aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2 mg of 4-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)pyrido(3,4-b)pyrazin-3(4H)-one as a light brown oily substance.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe resultant residue was charged with chloroform and water
  3. customthe aqueous layer was separated
  4. additionChloroform was added to the aqueous layer
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a698a0ce10304bcba2eed5aa75a2d3b7
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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