Tetrahydrofuran → 4-{[Cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoic acid

HRID 2091319Notes

Reaction equation

HRID 2091319 reaction equation
[CH:1]1([CH:7]([NH:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=2)[C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH:1]1([CH:7]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=2)[C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 66778069Methyl 4-{[cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoate

Product 1

HCID 667781814-{[Cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoate (1.31 g) synthesized above, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred overnight with heating under reflux. 1N Aqueous sodium hydroxide solution (5 mL) was additionally added, and the mixture was further stirred with heating under reflux for 7 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 brown 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 (804 mg, 64%) as a brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. stirringthe mixture was further stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 7 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 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
  14. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-21b10cd3a4f44529bc27fee407d327f7
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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