HCID 15491456, compound → 3-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamine

HRID 1858161Notes

Reaction equation

HRID 1858161 reaction equation
O[N:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=2)=[CH:3]1.[H][H]>[Pd].O>[NH2:11][C:7]1[N:6]=[C:5]2[C:4]([CH:12]3[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]3)=[CH:3][NH:2][C:10]2=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 15491456HCID 15491456, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 102202303-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 1 gm (3.15 mMol) 1-hydroxy-5-amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrrolo[3,2-b]pyridine (H) dihydrochloride and 0.20 gm 10% palladium on carbon in 10 mL demineralized water was hydrogenated at ambient temperature with an initial hydrogen pressure of 45 p.s.i. After four hours the reaction mixture was filtered and the filtrate treated with 6 mL 2N aqueous sodium hydroxide. After the addition of 0.2 mL tetrahydrofuran the reaction mixture was stirred for 3 hours and the resulting precipitate collected by filtration. The solid was dried under reduced pressure at 50° C. to provide 0.59 gm (94%) of the title compound.

Workup

  1. filtrationAfter four hours the reaction mixture was filtered
  2. additionthe filtrate treated with 6 mL 2N aqueous sodium hydroxide
  3. additionAfter the addition of 0.2 mL tetrahydrofuran the reaction mixture
  4. filtrationthe resulting precipitate collected by filtration
  5. customThe solid was dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-ae02f3d53e2742d891cef7a582017931
Source dataset
uspto-grants-2000_11
Patent number
US06150525

Reaction notes

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