N,N-Dimethylethylenediamine → HCID 14390342, compound

HRID 623060Notes

Reaction equation

HRID 623060 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.[C:24](N1C=CN=C1)([N:26]1[CH:30]=[CH:29][N:28]=[CH:27]1)=O.CN(C)CCN>O1CCCC1>[CH3:24][N:26]([CH3:27])[CH2:30][CH2:29][NH:28][C:19](=[O:21])[CH2:18][N:17]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[N:10]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:23])[F:22])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 15617192HCID 15617192, compound

Product 1

HCID 14390342HCID 14390342, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-[4-(trifluoromethyl)phenyl]-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0156 mole), 1,1'-carbonyldiimidazole (3.0 g, 0.0185 mole) and dry tetrahydrofuran (125 ml) was stirred at room temperature for 2 hours with nitrogen bubbling through it. The reaction mixture was then heated at 50° C. under nitrogen for 2 hours. The solution was cooled and a solution of N,N-dimethylethylenediamine (4.2 g, 0.047 mole) in tetrahydrofuran (5 ml) was added. The reaction mixture was stirred at room temperature overnight under nitrogen and evaporated under reduced pressure. The residue was triturated in water, and the solid was collected by filtration, washed once with water, twice with 5% potassium hydroxide solution and then twice again with water to yield 3.0 g (49%) of product. A 0.7-g sample of the solid was dissolved in hot isopropyl ether with a little isopropyl alcohol added to aid solubility, filtered, and cooled to room temperature to yield 0.4 g of a white solid, mp 196°-197.5° C.

Workup

  1. temperatureThe reaction mixture was then heated at 50° C. under nitrogen for 2 hours
  2. temperatureThe solution was cooled
  3. stirringThe reaction mixture was stirred at room temperature overnight under nitrogen
  4. customevaporated under reduced pressure
  5. customThe residue was triturated in water
  6. filtrationthe solid was collected by filtration
  7. washwashed once with water, twice with 5% potassium hydroxide solution

Sources & evidence

ORD record
ord-80e52424c6574f278ce959a2c829847c
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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