Dimethylamine → HCID 14390408, compound

HRID 1709577Notes

Reaction equation

HRID 1709577 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[C:22](N1C=CN=C1)([N:24]1C=CN=[CH:25]1)=O.CNC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([C@H:17]([CH3:21])[C:18]([N:24]([CH3:25])[CH3:22])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 14390428HCID 14390428, compound

Product 1

HCID 14390408HCID 14390408, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of (R)-2-(4-chlorophenyl)-α-methyl-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0166 mole), 1,1'-carbonyldiimidazole (2.69 g, 0.0166 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for 2.25 hours with a stream of nitrogen bubbling through it. A solution of dimethylamine in tetrahydrofuran (22 ml of a 2.29M solution, 0.050 mole) was added and the reaction mixture was heated at 45° C. for two days under nitrogen. The solvents were removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was washed twice with water, twice with a 5% potassium hydroxide solution and twice again with water. It was then dried over magnesium sulfate, charcoaled, filtered, and evaporated to a residue which was dissolved in hot isopropyl ether, filtered, and cooled to room temperature. The resulting solid was collected by filtration and dried under high vacuum at 50° C. to give 2.61 g (48%) of title compound, mp 124°-127° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe ethyl acetate layer was washed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  4. dry with materialIt was then dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to a residue which
  7. dissolutionwas dissolved in hot isopropyl ether
  8. filtrationfiltered
  9. temperaturecooled to room temperature
  10. filtrationThe resulting solid was collected by filtration
  11. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-6d0636668a07451cad1e7a386ba8a9da
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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