Sodium Bicarbonate → HCID 117989537, compound

HRID 2201366Notes

Reaction equation

HRID 2201366 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:10]([C:12]2[C:13]([S:18][CH2:19][CH3:20])=[N:14][CH:15]=[N:16][CH:17]=2)=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:13]1[C:12]([C:10]2[N:2]([CH3:1])[C:3]3=[N:4][CH:5]=[C:6]([C:21]([F:24])([F:23])[F:22])[CH:7]=[C:8]3[N:9]=2)=[CH:17][N:16]=[CH:15][N:14]=1)[CH3:20]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 118148713HCID 118148713, compound

Product 1

HCID 117989537HCID 117989537, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1.94 g of 4-ethylsulfanylpyrimidine-5-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide, 2.07 g of p-toluenesolufonic acid-hydrate and 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 mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 130 mg of 2-(4-ethylsulfanylpyrimidin-5-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 14).

Workup

  1. temperaturewas heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e946734c33184185bca1ada4c8d068d9
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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