Ethanol → HCID 66778447, compound

HRID 2091056Notes

Reaction equation

HRID 2091056 reaction equation
[CH:1]1([CH:7]([NH:19][C:20]2[N:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O1CCCC1>[CH:1]1([CH:7]([NH:19][C:20]2[N:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 66777011HCID 66777011, compound

Product 1

HCID 66778447HCID 66778447, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 6-{[cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}pyridine-3-carboxylate (547 mg) synthesized above, ethanol (10 mL) and tetrahydrofuran (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred overnight with heating under reflux. In addition, 1N aqueous sodium hydroxide solution (5.00 mL) was added, and the mixture was stirred with heating under reflux for 5 hr, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), and 1N hydrochloric acid (15 mL) was added at 0° C. The resulting precipitate was collected by filtration, and the obtained pale-brown solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (478 mg, 90%) as a pale-brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. stirringthe mixture was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 5 hr
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in water (20 mL)
  8. addition1N hydrochloric acid (15 mL) was added at 0° C
  9. filtrationThe resulting precipitate was collected by filtration
  10. dissolutionthe obtained pale-brown solid was dissolved in ethyl acetate
  11. washThe solution was washed with saturated brine
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8e9525dc0ab4d4ba36dda5e8e4fadb2
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…