Sodium ethoxide → HCID 18918975, compound

HRID 1291267Notes

Reaction equation

HRID 1291267 reaction equation
[O-]CC.[Na+].[Na].[C:6]([N:10]1[C:15](=[O:16])[C:14](Cl)=[C:13]([N:18]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30](=[O:38])[C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)[CH2:19][CH2:20][CH2:21][OH:22])[CH:12]=[N:11]1)([CH3:9])([CH3:8])[CH3:7]>C(O)C.O>[C:6]([N:10]1[C:15](=[O:16])[C:14]2[O:22][CH2:21][CH2:20][CH2:19][N:18]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:38])[C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)[C:13]=2[CH:12]=[N:11]1)([CH3:7])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 18919096HCID 18919096, compound

Product 1

HCID 18918975HCID 18918975, compoundYield 142.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

To a solution of sodium ethoxide in ethanol as prepared by dissolving sodium metal (6.5 mg) in ethanol (1 ml) was added a solution of 2-tert-butyl-4-chloro-5-[N-(4-(4-chlorobenzoyl)benzyl)-N-(3-hydroxypropyl)-amino]-3-(2H)-pyridazinone (91 mg) in ethanol (5 ml) and the mixture was refluxed for 46 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and saturated aqueous NaCl solution in that order and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=1:1→1:2) to provide the title compound as white powder (120 mg, yield 12%). 1H-NMR (CDC13) 8: 1.62(9H,s), 2.06(2H,q,J=6.2Hz), 3.55(2H,t,J=6.2Hz), 4.42(2H,t,J=6.2Hz), 4.55(2H,m), 7.32(1H,s), 7.41(2H,d,J=8.4Hz), 7.48(2H,d,J=8.4Hz), 7.76(2H,d,J=8.4Hz), 7.81(2H,d,J=8.4Hz).

Workup

  1. temperaturethe mixture was refluxed for 46 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated aqueous NaCl solution in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (developer; n-hexane: ethyl acetate=1:1→1:2)

Sources & evidence

ORD record
ord-a2093b97754f4efa9dd9ac0011129c66
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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