Dimethylamine → 2-{2-[4-(1-Dimethylamino-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

HRID 1425773Notes

Reaction equation

HRID 1425773 reaction equation
Br[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:29])[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=3)[CH:14]=[N:13]2)=[C:6]([CH3:30])[CH:5]=1)[CH3:3].[CH3:31][NH:32][CH3:33]>C(Cl)Cl>[CH3:31][N:32]([CH3:33])[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:29])[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=3)[CH:14]=[N:13]2)=[C:6]([CH3:30])[CH:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 866955602-{2-[4-(1-Bromo-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Product 1

HCID 717309172-{2-[4-(1-Dimethylamino-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-[4-(1-Bromo-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 10d, 1.55 g, 3.28 mmol) in CH2Cl2 (5 mL) is added a solution of dimethylamine (2 M in THF, 4.9 mL, 9.8 mmol). The reaction mixture is stirred overnight at room temperature. After dilution with CH2Cl2, the mixture is washed with aqueous NaHCO3 solution. The organic layer is dried over MgSO4 and evaporated under reduced pressure. The crude product is purified via reverse phase HPLC chromatography (Phenomenex Gemini C18, gradient 30%→95% methanol in water+0.1% NH4OH, 120 mL/min).

Workup

  1. washAfter dilution with CH2Cl2, the mixture is washed with aqueous NaHCO3 solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe crude product is purified via reverse phase HPLC chromatography (Phenomenex Gemini C18, gradient 30%→95% methanol in water+0.1% NH4OH, 120 mL/min)

Sources & evidence

ORD record
ord-d509285c26d740368ce2bfda5b76cc2d
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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