Water → 4-{N-(6-Chloro-3-pyridazinyl)-N-methyl-5-aminopentan-1-oxy}benzaldehyde

HRID 1792754Notes

Reaction equation

HRID 1792754 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[N:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=2)=[CH:6][CH:5]=1.[CH3:25]I.O>C1COCC1>[Cl:3][C:4]1[N:9]=[N:8][C:7]([N:10]([CH3:25])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH:21]=[O:22])=[CH:23][CH:24]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 220242754-[[5-[(6-Chloro-3-pyridazinyl)amino]pentyl]oxy]benzaldehyde

Product 1

HCID 220242564-{N-(6-Chloro-3-pyridazinyl)-N-methyl-5-aminopentan-1-oxy}benzaldehydeYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (10 mg, 0.24 mmol) was added to a solution of 4-{N-(6-Chloro-3-pyridazinyl)-5-aminopentan-1-oxy}benzaldehyde (51 mg, 0.16 mmol) in THF (3.5 ml) and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (50 μl, 0.8 mmol) was added to the reaction mixture and the suspension was stirred at room temperature for 48 hours. The reaction mixture was poured into water (1.5 ml) and concentrated under reduced pressure. The residue was partitioned between water (2 ml) and ethyl acetate (40 ml), shaken thoroughly and the organic layer was separated, dried and evaporated to give a yellow solid. Purification by chromatography on silica gel (6 g, 30% ethyl acetate/hexane) gave 4-{N-(6-Chloro-3-pyridazinyl)-N-methyl-5-aminopentan-1-oxy}benzaldehyde (16 mg, 30%) as a pale yellow oil.

Workup

  1. stirringthe suspension was stirred at room temperature for 48 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between water (2 ml) and ethyl acetate (40 ml)
  4. stirringshaken thoroughly
  5. customthe organic layer was separated
  6. customdried
  7. customevaporated
  8. customto give a yellow solid
  9. customPurification by chromatography on silica gel (6 g, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-13dd3bfb9a69454a9e9066abb2cd96db
Source dataset
uspto-grants-2006_07
Patent number
US07078403B1

Reaction notes

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