Sodium Hydroxide → HCID 69430520, compound

HRID 1269975Notes

Reaction equation

HRID 1269975 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=O)[CH2:21][CH3:22])[CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[C:11]([O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][CH2:20][CH2:21][CH3:22])[CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69433339HCID 69433339, compound

Product 1

HCID 69430520HCID 69430520, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen, N-[cis-3-[(4-methoxy-1H-indazol-5-yl)oxy]cyclohexyl]propanamide (141 mg, 0.444 mmol) was dissolved in tetrahydrofuran (7 ml), followed by adding thereto lithium aluminum hydride (84 mg, 2.22 mmol), and the resulting mixture was stirred with heating under reflux for about 2 hours. Under ice-cooling, the reaction solution was diluted with tetrahydrofuran, and water (84 μl) was added thereto and stirred, and then a 4N-aqueous sodium hydroxide solution (84 μl) and water (250 μl) were added thereto and stirred. The solid was filtered off and the solvent was distilled off under reduced pressure. The resulting concentration residue was purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/2, 100/5) to obtain N-[cis-3-[(4-methoxy-1H-indazol-5-yl)oxy]cyclohexyl]-N-propylamine (57 mg, yield 42.3%) as colorless tar.

Workup

  1. additionby adding
  2. temperaturewith heating
  3. temperatureunder reflux for about 2 hours
  4. temperatureUnder ice-cooling
  5. additionwas added
  6. stirringstirred
  7. filtrationThe solid was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. concentrationThe resulting concentration residue
  10. customwas purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/2, 100/5)

Sources & evidence

ORD record
ord-908ec675f3a24a42b2d9082dc6198f52
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…