Methyl 3-[2-({4-[(2-methoxypyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoate → Methyl 3-({6-[(2-methoxypyridin-4-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

HRID 1843718Notes

Reaction equation

HRID 1843718 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=O)[CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=3)[C:23]([O:25][CH3:26])=[O:24])=[C:12]([NH:31][CH3:32])[CH:11]=2)[CH:6]=[CH:5][N:4]=1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]3[N:16]=[C:17]([CH2:18][O:19][C:20]4[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=4)[C:23]([O:25][CH3:26])=[O:24])[N:31]([CH3:32])[C:12]=3[CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 66705881Methyl 3-[2-({4-[(2-methoxypyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoate

Product 1

HCID 66705919Methyl 3-({6-[(2-methoxypyridin-4-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoateYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 3-[2-({4-[(2-methoxypyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoate produced in Example (16e) (4.52 g, 10.3 mmol) and acetic acid (50 mL) was stirred at 80° C. for two hours. The reaction mixture was concentrated and then water (100 mL) and sodium bicarbonate were added, followed by extraction with ethyl acetate (100 mL). The organic layer was washed with a saturated sodium bicarbonate aqueous solution (100 mL) twice and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (hexane/ethyl acetate, 1:1) to obtain the title compound (3.10 g, 72%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (100 mL) and sodium bicarbonate were added
  3. extractionfollowed by extraction with ethyl acetate (100 mL)
  4. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution (100 mL) twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-5ea0b29fc36545e89b55c41a3a1e4a63
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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