Benzaldehyde → HCID 9797155, compound

HRID 1075567Notes

Reaction equation

HRID 1075567 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>CO>[CH2:18]([NH:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 102202303-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamine

Product 1

HCID 9797155HCID 9797155, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 0.25 gm (1.09 mMol) 5-amino-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine, 0.5 gm molecular sieves, and 0.22 mL (2.17 mMol) benzaldehyde in 10 mL methanol was stirred at 40° C. for 5 hours. The reaction mixture was then cooled to room temperature and then 0.124 gm (3.27 mMol) sodium borohydride were added. The reaction mixture was then stirred for 30 minutes at room temperature and then the reaction mixture quenched with 1N sodium hydroxide. The reaction mixture was concentrated under reduced pressure and then the aqueous residue was extracted well with 3:1 chloroform:isopropanol. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing 0-10% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. stirringThe reaction mixture was then stirred for 30 minutes at room temperature
  3. customthe reaction mixture quenched with 1N sodium hydroxide
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionthe aqueous residue was extracted well with 3:1 chloroform
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washeluting with dichloromethane containing 0-10% methanol
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6d59ac94e914ddf84a68fe680786cc3
Source dataset
uspto-grants-1999_05
Patent number
US05905084

Reaction notes

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