Methanol → HCID 46909009, compound

HRID 1843726Notes

Reaction equation

HRID 1843726 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=4)[C:22]([OH:24])=[O:23])[N:14]([CH3:28])[C:13]=3[CH:29]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:32][OH:33]>C(O)C.O>[CH3:32][O:33][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=4)[C:22]([OH:24])=[O:23])[N:14]([CH3:28])[C:13]=3[CH:29]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 86661631HCID 86661631, compound

Product 1

HCID 46909009HCID 46909009, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3-({6-[(6-chloropyridin-3-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoic acid produced in Example (18e) (0.40 g, 0.98 mmol) and sodium hydride (63%, 0.372 g, 9.76 mmol) in methanol (9.8 mL) was heated under reflux under microwave irradiation for two hours. After leaving to cool, water was added to the reaction mixture. This aqueous solution was washed with hexane five times and neutralized by adding 1 M hydrochloric acid. The precipitated solid was collected by filtration to obtain the crude title compound. A suspension of the crude title compound in ethanol (5 mL) and water (5 mL) was heated under reflux for two hours and left to cool. Then, the precipitated solid was collected by filtration to obtain the title compound (0.312 g, 79%) as a white solid.

Workup

  1. temperatureunder reflux under microwave irradiation for two hours
  2. customAfter leaving
  3. temperatureto cool
  4. washThis aqueous solution was washed with hexane five times
  5. additionby adding 1 M hydrochloric acid
  6. filtrationThe precipitated solid was collected by filtration
  7. customto obtain the crude title compound
  8. temperaturewas heated
  9. temperatureunder reflux for two hours
  10. waitleft
  11. temperatureto cool
  12. filtrationThen, the precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ac13a3939db641d59f4711319f5766f6
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

Loading…