Sodium Bicarbonate → HCID 117988476, compound

HRID 2201358Notes

Reaction equation

HRID 2201358 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[S:18][CH2:19][CH3:20])=O)=[CH:7][C:6]([C:21]([F:24])([F:23])[F:22])=[CH:5][N:4]=1.C(=O)(O)[O-].[Na+]>CN1C(=O)CCC1>[CH2:19]([S:18][C:17]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[C:10]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:21]([F:24])([F:23])[F:22])[CH:7]=[C:8]2[N:9]=1)[CH3:20]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 118148703HCID 118148703, compound

Product 1

HCID 117988476HCID 117988476, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 700 mg of 4-ethylsulfanylpyridine-3-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide, 704 mg of p-toluenesolufonic acid-hydrate and 3.5 ml of NMP 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 650 mg of 2-(4-ethylsulfanylpyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 9).

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-53d9867a8022418aa7ef87bb2faa0a61
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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