Dimethylformamide → 2,6,7-trimethyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine

HRID 1245901Notes

Reaction equation

HRID 1245901 reaction equation
C[N:2](C)C=O.Cl[C:7]1[C:12]([N+:13]([O-])=O)=[C:11](Cl)[C:10]([CH3:17])=[C:9]([CH3:18])[N:8]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH2:31])[CH:20]=1.[CH2:32](N(CC)CC)[CH3:33]>>[CH3:32][C:33]1[N:31]([CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)[C:11]2[C:10]([CH3:17])=[C:9]([CH3:18])[N:8]=[C:7]([NH2:2])[C:12]=2[N:13]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridineHCID 219130212-(3-Pyridin-3-ylpropoxy)ethanamine

Product 1

HCID 100885762,6,7-trimethyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine

Conditions

Temperature
45 °C

Procedure

Anhydrous N,N-dimethylformamide (200 ml), anhydrous triethylamine (12.1 ml), and 2,4-dichloro-5,6-dimethyl-3-nitropyridine (16.05 g) were combined and 2-(3-pyridin-3-ylpropoxy)ethylamine (14.4 g) was then added with stirring. The pale yellow reaction mixture was heated to 45° C. under a nitrogen atmosphere for 1 hour. HPLC analysis indicated that the reaction was sufficiently complete to proceed. The reaction mixture was allowed to cool and the solvent was removed under reduced pressure. The resulting oil was dissolved in ethyl acetate and washed twice: once with a saturated aqueous solution of ammonium chloride and once with water. The organic layer was then extracted 3 times with brine, dried with magnesium sulfate, and concentrated under reduced pressure. The product was passed through a silica gel column using 90/10 ethyl acetate/hexane as the eluant. The resulting oil was dried under vacuum at 60° C. for 2 hours. NMR analysis indicated sufficient purity for use of the product in the next step.

Workup

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe resulting oil was dissolved in ethyl acetate
  4. washwashed twice
  5. extractionThe organic layer was then extracted 3 times with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil was dried under vacuum at 60° C. for 2 hours

Sources & evidence

ORD record
ord-434969423a3c476c96a62fea7848db0f
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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