Dimethylformamide → HCID 117988840, compound

HRID 2201362Notes

Reaction equation

HRID 2201362 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:17]=2[S:18][CH2:19][CH3:20])=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>[CH2:19]([S:18][C:17]1[CH:16]=[C:15]([C:21]([F:24])([F:23])[F:22])[N:14]=[CH:13][C:12]=1[C:10]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:25]([F:28])([F:27])[F:26])[CH:7]=[C:8]2[N:9]=1)[CH3:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 118148693HCID 118148693, compound

Product 1

HCID 117988840HCID 117988840, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 786 mg of 4-ethylsulfanyl-6-trifluoromethylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide, 704 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 716 mg of 2-(4-ethylsulfanyl-6-trifluoromethylpyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 12).

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-e081c612300f4d1891e6ed4102c42591
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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