Hydrochloric Acid → HCID 68523043, compound

HRID 1932489Notes

Reaction equation

HRID 1932489 reaction equation
C(O[C:4](=[O:26])[CH2:5][N:6]([C:23](=[O:25])[CH3:24])[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl.[CH2:30]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[C:31]1[CH:39]=[CH:38][C:37]2[O:36][CH2:35][O:34][C:33]=2[CH:32]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>C(O)C.CN(C=O)C.O>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][C:10]2[CH:9]=[CH:8][C:7]([N:6]([CH2:5][C:4]([N:43]3[CH2:44][CH2:45][N:40]([CH2:30][C:31]4[CH:39]=[CH:38][C:37]5[O:36][CH2:35][O:34][C:33]=5[CH:32]=4)[CH2:41][CH2:42]3)=[O:26])[C:23](=[O:25])[CH3:24])=[CH:12][CH:11]=2)=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 944261-PiperonylpiperazineHCID 90971607HCID 90971607, compound

Product 1

HCID 68523043HCID 68523043, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl{acetyl[4-(5-nitropyridin-2-yloxy)phenyl]amino}acetate (2.30 g, 6.40 mmol) in ethanol (50 mL) was added 5 M aqueous sodium hydroxide (1.92 mL, 9.60 mmol), and the resulting solution was stirred at room temperature for 30 minutes. To this reaction solution were added 5 M hydrochloric acid (2 mL) and water, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, evaporated, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1), to thereby yield 1.68 g of an oil. To a solution of this oil in DMF (10 mL) were added 1-piperonylpiperazine (1.29 g, 5.86 mmol), triethylamine (1.85 mL, 13.3 mmol) and diethyl cyanophosphonate (1.07 mL, 6.36 mmol), and the resulting solution was stirred for 1 hour at room temperature. To this reaction solution was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, evaporated, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1), to thereby yield 2.21 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
  6. stirringthe resulting solution was stirred for 1 hour at room temperature
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-2d689d7c53e245729f8aeda8f42891ff
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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