Phosphorus oxychloride → HCID 117988658, compound

HRID 2201370Notes

Reaction equation

HRID 2201370 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH:9][C:10]([C:12]2[CH:17]=[C:16]([Cl:18])[N:15]=[N:14][C:13]=2[S:19][CH2:20][CH3:21])=O)=[CH:7][C:6]([C:22]([F:25])([F:24])[F:23])=[CH:5][N:4]=1.P(Cl)(Cl)(Cl)=O.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[Cl:18][C:16]1[N:15]=[N:14][C:13]([S:19][CH2:20][CH3:21])=[C:12]([C:10]2[N:2]([CH3:1])[C:3]3=[N:4][CH:5]=[C:6]([C:22]([F:25])([F:24])[F:23])[CH:7]=[C:8]3[N:9]=2)[CH:17]=1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 118148716HCID 118148716, compound

Product 1

HCID 117988658HCID 117988658, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 900 mg of 6-chloro-3-ethylsulfanylpyridazine-4-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl)-amide, 3.5 ml of phosphorus oxychloride, 592 mg of N,N-diisopropylethylamine and 15 ml of toluene was heated and stirred at 100° C. for 4 hours. Water was poured to the cooled reaction mixture, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, extracted with t-butyl methyl ether. The organic layer was washed with water, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 534 mg of 2-(6-chloro-3-ethylsulfanylpyridazin-4-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound of Present Invention 16).

Workup

  1. temperaturewas heated
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with t-butyl methyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-079aef5a9b6847eb84cf5adf662df04f
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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