Hydrochloric Acid → 1-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochloride

HRID 2378952Notes

Reaction equation

HRID 2378952 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1.[ClH:24].O1CCOCC1>CO>[ClH:24].[ClH:24].[NH:14]1[CH2:13][CH2:12][CH:11]([N:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:10][C:2]2=[O:1])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 22293220tert-butyl 4-{2-oxo-1H,2H,3H-imidazo[4,5-b]pyridin-1-yl}piperidine-1-carboxylate

Product 1

HCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (5.97 g, 18.75 mmol) was dissolved in methanol (180 ml). 4M Hydrogen chloride in 1,4-dioxane (50 ml, 200 mmol) was added to the mixture. Reaction stirred at room temperature for 18 hours. Solids were filtered off and washed with methanol. Solids were collected and dried in vacuo. Title compound was obtained as white solid in 87% yield. MS (M+H)+=219.1.

Workup

  1. customReaction
  2. filtrationSolids were filtered off
  3. washwashed with methanol
  4. customSolids were collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-39362ede2ce84ee29068a99ab1b47fe0
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

Loading…