Hydrazine hydrate (1:1) → HCID 22106042, compound

HRID 1456379Notes

Reaction equation

HRID 1456379 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][CH2:22][CH2:23][CH2:24][N:25]3C(=O)C4=CC=CC=C4C3=O)[CH:16]=2)=[C:7]([NH:36][C:37]([NH:39][C:40]2[C:45]([CH:46]([CH3:48])[CH3:47])=[CH:44][CH:43]=[CH:42][C:41]=2[CH:49]([CH3:51])[CH3:50])=[O:38])[C:6]1=[O:52])[CH2:2][CH2:3][CH3:4].O.NN>C(O)C>[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][CH2:22][CH2:23][CH2:24][NH2:25])[CH:16]=2)=[C:7]([NH:36][C:37]([NH:39][C:40]2[C:41]([CH:49]([CH3:50])[CH3:51])=[CH:42][CH:43]=[CH:44][C:45]=2[CH:46]([CH3:48])[CH3:47])=[O:38])[C:6]1=[O:52])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22106191HCID 22106191, compound

Product 1

HCID 22106042HCID 22106042, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[1-butyl-4-{3-(3-phthalimidopropoxy)phenyl}-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea (157 mg, 0.22 mmol) in ethanol (10 ml) was added hydrazine monohydrate (100 mg, 2 mmol), and the mixture was stirred at room temperature for 3 hours. The precipitates were removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue was added methylene chloride, and the insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% methanol in chloroform) to give the title compound (58 mg, 0.10 mmol).

Workup

  1. customThe precipitates were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added methylene chloride
  4. customthe insoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (10% methanol in chloroform)

Sources & evidence

ORD record
ord-d3d49e350fb74dc695ff4badf3a781ce
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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