N,N-Dimethylethylenediamine → HCID 14390342, compound

HRID 2351719Notes

Reaction equation

HRID 2351719 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 under 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-dimethylethyl-enediamine (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 colleced 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 colleced by filtration
  7. washwashed once with water, twice with 5% potassium hydroxide solution

Sources & evidence

ORD record
ord-48c50d0b291e49f8807e4966286de424
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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