Phosphorus oxychloride → (2-Chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yl)-dipropylamine

HRID 2235567Notes

Reaction equation

HRID 2235567 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5]1[C:10]2[N:11]([CH3:15])[C:12](=O)[NH:13][C:9]=2[CH:8]=[CH:7][N:6]=1)[CH2:2][CH3:3].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:12]1[N:11]([CH3:15])[C:10]2[C:5]([N:4]([CH2:16][CH2:17][CH3:18])[CH2:1][CH2:2][CH3:3])=[N:6][CH:7]=[CH:8][C:9]=2[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 685842814-Dipropylamino-3-methyl-1,3-dihydroimidazo[4,5-c]pyridin-2-one

Product 1

HCID 68582019(2-Chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yl)-dipropylamine

Procedure

A solution of 0.91 g (3.66 mmol) of 4-dipropylamino-3-methyl-1,3-dihydroimidazo[4,5-c]pyridin-2-one in 30 mL of phosphorous oxychloride was heated at 100° C. overnight and concentrated in vacuo. The thus obtained residue was quenched with water, adjusted with aqueous sodium bicarbonate to pH 5, and extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The thus obtained residue was triturated with acetonitrile, filtered, and the filtrate, which contained the desired product, was concentrated in vacuo. The residue thus obtained (0.18 g, 18%) was used in the next reaction without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe thus obtained residue was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe thus obtained residue was triturated with acetonitrile
  8. filtrationfiltered
  9. concentrationwas concentrated in vacuo
  10. customThe residue thus obtained (0.18 g, 18%)
  11. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-481ae704dc264cc5b158c3786b29df36
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

Loading…