Hydrochloric Acid → 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

HRID 1064409Notes

Reaction equation

HRID 1064409 reaction equation
Cl.[NH2:2][C:3]1[C:8]2[N:9]=[C:10]([CH3:19])[N:11]([CH2:12][CH2:13][CH2:14][NH:15]C(=O)C)[C:7]=2[C:6]([CH3:20])=[C:5]([CH3:21])[N:4]=1>C(O)C>[NH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:7]2[C:6]([CH3:20])=[C:5]([CH3:21])[N:4]=[C:3]([NH2:2])[C:8]=2[N:9]=[C:10]1[CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 10192920N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]acetamide

Product 1

HCID 219460311-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amineYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Concentrated hydrochloric acid (5 mL) was slowly added to a solution of N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]acetamide (15.94 g, 57.9 mmol) in absolute ethanol (100 mL). A precipitate formed immediately and the mixture thickened. Ethanol (50 mL) was added followed by the addition of concentrated hydrochloric acid (119.5 mL). The reaction mixture was heated at reflux for 2 days. The solvents were removed under reduced pressure. Water (250 mL) was added to the residue, solid potassium carbonate was added until the pH reached 7 at which time chloroform (250 mL) was added. Sodium carbonate addition was resumed until the pH reached 10, then 50% sodium hydroxide was added until the pH reached 14. The mixture was diluted with additional chloroform (500 mL) and then stirred at ambient temperature for 2 days. The organic layer was separated, dried with magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from acetonitrile to provide 8.42 g of 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine as an off-white crystalline solid, m.p. 191.5-200° C. Analysis: Calculated for C12H19N5.0.25 H2O: % C, 60.61; % H, 8.26; % N, 29.45. Found % C, 60.50; % H, 8.28; % N, 29.57.

Workup

  1. customA precipitate formed immediately
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 2 days
  4. customThe solvents were removed under reduced pressure
  5. additionWater (250 mL) was added to the residue, solid potassium carbonate
  6. additionwas added until the pH
  7. additionwas added
  8. additionSodium carbonate addition
  9. addition50% sodium hydroxide was added until the pH
  10. additionThe mixture was diluted with additional chloroform (500 mL)
  11. customThe organic layer was separated
  12. dry with materialdried with magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8d1aef5d540145efbd62df9bd1f09aa9
Source dataset
uspto-grants-2005_11
Patent number
US06969722B2

Reaction notes

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