Pyridine → HCID 66664493, compound

HRID 2390479Notes

Reaction equation

HRID 2390479 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.[CH3:14][C:15]1[CH:23]=[N:22][CH:21]=[CH:20][C:16]=1[C:17](O)=O.CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[CH3:1][N:2]1[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:13])([F:11])[F:12])[CH:7]=[C:8]2[N:9]=[C:17]1[C:16]1[CH:20]=[CH:21][N:22]=[CH:23][C:15]=1[CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15020033-Methyl-isonicotinic acidHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 66664493HCID 66664493, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.40 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.32 g of 3-methylisonicotinic acid, 0.44 g of WSC and 10 ml of pyridine was stirred for 5 hours at 120° C. The reaction mixture was cooled down to room temperature. Into the reaction mixture was poured water, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, then, concentrated under reduced pressure. To the residue was added a mixture of 0.60 g of p-toluenesulfonic acid monohydrate and 10 ml of toluene, and the mixture was stirred for 1 hour at 120° C. Toluene was distilled off from this mixture. To the residue was added 10 ml of phenyl bromide, and the mixture was stirred for 4 hours at 150° C. The reaction mixture was cooled down to room temperature. Into the reaction mixture was poured water, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.14 g of 3-methyl-2-(3-methylpyridin-4-yl-)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as present active compound 216).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added
  6. additiona mixture of 0.60 g of p-toluenesulfonic acid monohydrate and 10 ml of toluene
  7. stirringthe mixture was stirred for 1 hour at 120° C
  8. distillationToluene was distilled off from this mixture
  9. additionTo the residue was added 10 ml of phenyl bromide
  10. stirringthe mixture was stirred for 4 hours at 150° C
  11. temperatureThe reaction mixture was cooled down to room temperature
  12. additionInto the reaction mixture was poured water
  13. extractionthe mixture was extracted three times with ethyl acetate
  14. dry with materialThe organic layer was dried over magnesium sulfate
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9559be7f29634ed294212450ed73f737
Source dataset
uspto-grants-2012_09
Patent number
US08273764B2

Reaction notes

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