Dimethylamine → HCID 14390408, compound

HRID 622026Notes

Reaction equation

HRID 622026 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×

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° L 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. temperaturethe reaction mixture was heated at 45° L C
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. washThe ethyl acetate layer was washed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  5. dry with materialIt was then dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a residue which
  8. dissolutionwas dissolved in hot isopropyl ether
  9. filtrationfiltered
  10. filtrationThe resulting solid was collected by filtration
  11. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-4ee5579ff7e84320b3494b0cf5f698ce
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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