p-Toluenesulfonic acid → 1-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)-4-propylpyrrolidin-2-one

HRID 2043606Notes

Reaction equation

HRID 2043606 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH3:17])[CH2:12][C:11]2=[O:18])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+].CCOC(C)=O>C(OC)(OC)OC>[N:1]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[N:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH3:17])[CH2:12][C:11]2=[O:18])[CH:19]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 577430941-{[(3-Aminopyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one

Product 1

HCID 159798021-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)-4-propylpyrrolidin-2-oneYield 302.4%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

A solution of 1-{[(3-aminopyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one x78 (1 eq, 1.6 mmol, 300 mg), and para-toluenesulfonic acid (0.32 mmol, 0.2 eq, 42 mg) in trimethyl orthoformate (15 ml) is allowed to react at room temperature for 3 days. After hydrolysis (20 ml of saturated NaHCO3), extraction with AcOEt (2×10 ml), drying of the cumulated organic layers over MgSO4, and filtration, the volatiles are removed under reduced pressure and the crude material is purified by preparative chromatography affording 250 mg of 1-(3H-imidazo[4,5-b]pyridin-3-ylmethyl)-4-propylpyrrolidin-2-one 268.

Workup

  1. customto react at room temperature for 3 days
  2. dry with materialdrying of the cumulated organic layers over MgSO4, and filtration
  3. customthe volatiles are removed under reduced pressure
  4. customthe crude material is purified by preparative chromatography

Sources & evidence

ORD record
ord-157b688784f04db19524e6142c8f4315
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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