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

HRID 2091252Notes

Reaction equation

HRID 2091252 reaction equation
[Br: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.[OH-].[Li+].C(O)C>O1CCCC1>[Br: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 Hydroxide3×HCID 86662738Methyl 4-{[(5-bromo-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoate

Product 1

HCID 866627394-{[(5-Bromo-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of methyl 4-{[(5-bromo-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoate (1.86 g) synthesized above in tetrahydrofuran was added 2N lithium hydroxide aqueous solution (10.2 mL), and the mixture was stirred with heating under reflux for 2 hr. A 4N aqueous lithium hydroxide solution (5.10 mL) was additionally added, and the mixture was stirred with heating under reflux for 4 hr. A 4N aqueous lithium hydroxide solution (5.10 mL) and ethanol (20 mL) were further added, and the mixture was stirred with heating under reflux for 4 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (61.2 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (1.74 g, 96%) as a pale-brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. stirringthe mixture was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 4 hr
  6. stirringthe mixture was stirred
  7. temperaturewith heating
  8. temperatureunder reflux for 4 hr
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe residue was dissolved in water (40 mL)
  11. addition1N hydrochloric acid (61.2 mL) was added at 0° C
  12. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-1ded841afe414c82ab074f3c4dd24f62
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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