Hydrazine hydrate (1:1) → HCID 18467162, compound

HRID 2229401Notes

Reaction equation

HRID 2229401 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:30]([CH2:36][N:37]3C(=O)C4=CC=CC=C4C3=O)=[CH:29][C:28]=2[CH:48]([CH3:50])[CH3:49])=[O:25])[C:6]1=[O:51])[CH2:2][CH2:3][CH3:4].C(O)C.C(Cl)(Cl)Cl.O.NN>O>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:28]([CH:48]([CH3:49])[CH3:50])=[CH:29][C:30]([CH2:36][NH2:37])=[CH:31][C:32]=2[CH:33]([CH3:35])[CH3:34])=[O:25])[C:6]1=[O:51])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)2×HCID 18467148HCID 18467148, compoundHCID 21889567Chloroform ethanol

Product 1

HCID 18467162HCID 18467162, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-(2,6-diisopropyl-4-phthalimidomethylphenyl)-urea (393 mg, 0.57 mmol) in a mixed solvent of ethanol/chloroform (10 ml) is added hydrazine monohydrate (0.033 ml, 0.68 mmol) at room temperature, and the mixture is stirred at room temperature for 2 hours. To the mixture is further added hydrazine monohydrate (0.14 ml, 3.4 mmol), and the mixture is stirred at room temperature for 4 days. To the mixture is added water, and the mixture is extracted with ethyl acetate. The organic layer is washed twice with an aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give the title compound (256 mg, 0.46 mmol).

Workup

  1. stirringthe mixture is stirred at room temperature for 4 days
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed twice with an aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0aa25bc2cd9c44308ee855afd3c7c6e8
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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