Triethylamine → Ethyl 2-[5-bromo-4-(4-ethoxy-3-methoxybenzylamino)-6-oxopyridazin-1(6H)-yl]acetate

HRID 2092079Notes

Reaction equation

HRID 2092079 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](=[O:9])[C:7]=1[Br:8].[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:22][NH2:23])C.[CH2:29](N(CC)CC)C.C(OCC)(=O)C>O1CCOCC1.O>[Br:8][C:7]1[C:6](=[O:9])[N:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:4]=[CH:3][C:2]=1[NH:23][CH2:22][C:21]1[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH3:29])=[C:19]([O:18][CH3:16])[CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6486613(3-Ethoxy-4-methoxyphenyl)methanamineHCID 59574424Ethyl 2-(4,5-dibromo-6-oxopyridazin-1(6H)-yl)acetate

Product 1

HCID 59574404Ethyl 2-[5-bromo-4-(4-ethoxy-3-methoxybenzylamino)-6-oxopyridazin-1(6H)-yl]acetateYield 98%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Ethyl 2-(4,5-dibromo-6-oxopyridazin-1(6H)-yl)acetate (500 mg, 1.47 mmol) and 3-ethoxy-4-methoxybenzylamine (960 mg, 4.41 mmol) in 1,4-dioxane-water (1:1, 5 mL) were stirred with triethylamine (0.615 mL) at 100° C. for 2.5 hours. After cooling, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The resulting residue was purified by silica gel chromatography (chloroform/2-propanol=20/1) to give the desired product (640 mg, 98% yield).

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation
  5. customThe resulting residue was purified by silica gel chromatography (chloroform/2-propanol=20/1)

Sources & evidence

ORD record
ord-0307eab1e9d14161a0f584c830d888b5
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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