Ethanol → 4-{[(5-Chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoic acid

HRID 2091263Notes

Reaction equation

HRID 2091263 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:29])=[C:9]([CH:11]([NH:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[O:10][C:5]2=[CH:4][CH:3]=1.C(O)C.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:29])=[C:9]([CH:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[O:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 86662746Methyl 4-{[(5-chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoate

Product 1

HCID 866627474-{[(5-Chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-{[(5-chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoate (1.31 g) synthesized above, ethanol (20 mL) and tetrahydrofuran (20 mL) was added 1N lithium hydroxide aqueous solution (20 mL), and the mixture was stirred with heating under reflux for 3 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (20 mL) was added at 0° C. The resulting precipitate was collected by filtration and the obtained solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (1.21 g, 96%) as a pale-yellow solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (40 mL)
  5. addition1N hydrochloric acid (20 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration
  7. dissolutionthe obtained solid was dissolved in ethyl acetate
  8. washThe solution was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-99c67d7d0f684cac942b117453f36945
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…