1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 533600Notes

Reaction equation

HRID 533600 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[CH2:14]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=O)[CH:15]=[CH2:16].CCN=C=NCCCN(C)C>C1(C)C(C)=CC=CC=1>[CH2:14]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]2[N:9]=1)[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2646962-Allylsulfanylbenzoic acidHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 867081952-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineYield 47.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-allylsulfanylbenzoic acid (1.46 g), WSC (1.06 g), and xylene (10 ml) was stirred with heating at 145° C. for 3 hours. After the mixture was evaporated to remove xylene, acetic acid (10 ml) was added thereto, and stirred with heating at 120° C. for further 1 hour. To the reaction mixture cooled to room temperature, 5 mol/l of aqueous sodium hydroxide solution was added to neutralize, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.83 g of 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 10).

Workup

  1. customAfter the mixture was evaporated
  2. customto remove xylene, acetic acid (10 ml)
  3. additionwas added
  4. stirringstirred
  5. temperaturewith heating at 120° C. for further 1 hour
  6. temperatureTo the reaction mixture cooled to room temperature
  7. addition5 mol/l of aqueous sodium hydroxide solution was added
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1beabfb146994d988cb9668b57920613
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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