Dimethylformamide → HCID 117988884, compound

HRID 2201350Notes

Reaction equation

HRID 2201350 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:10]([C:12]2[C:13]([S:22][CH2:23][CH3:24])=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=O)=[CH:7][C:6]([C:25]([F:28])([F:27])[F:26])=[CH:5][N:4]=1.CN(C=O)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:23]([S:22][C:13]1[C:12]([C:10]2[N:2]([CH3:1])[C:3]3=[N:4][CH:5]=[C:6]([C:25]([F:28])([F:27])[F:26])[CH:7]=[C:8]3[N:9]=2)=[CH:17][CH:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[N:14]=1)[CH3:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 118148701HCID 118148701, compound

Product 1

HCID 117988884HCID 117988884, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 703 mg of 2-ethylsulfanyl-6-trifluoromethylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide, 630 mg of p-toluenesolufonic acid-hydrate, 2.5 ml of DMF and 0.5 ml of toluene was heated and stirred at 150° C. for 2 hours. A saturated aqueous sodium bicarbonate solution was poured to the cooled reaction mixture, and the precipitated solid was filtered. The resulting solid was washed with water and n-hexane, and then dried to obtain 616 mg of 2-(2-ethylsulfanyl-6-trifluoromethylpyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 4).

Workup

  1. temperaturewas heated
  2. filtrationthe precipitated solid was filtered
  3. washThe resulting solid was washed with water and n-hexane
  4. customdried

Sources & evidence

ORD record
ord-88580f52e87e41a78bc4f11f7a20d450
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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