Triethylamine → HCID 58158935, compound

HRID 453085Notes

Reaction equation

HRID 453085 reaction equation
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:11]=[C:10]([C:12]([OH:14])=O)[N:9]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][N:16]=2)[N:8]=1.C(N(CC)CC)C.[NH2:30][C:31]1[C:39]([Cl:40])=[CH:38][C:37]([Cl:41])=[CH:36][C:32]=1[C:33](O)=[O:34]>C(#N)C.O>[Br:6][C:7]1[CH:11]=[C:10]([C:12]2[O:14][C:33](=[O:34])[C:32]3[CH:36]=[C:37]([Cl:41])[CH:38]=[C:39]([Cl:40])[C:31]=3[N:30]=2)[N:9]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][N:16]=2)[N:8]=1

Participants

7

Reactant 4

HCID 8471Triethylamine3×HCID 31297Methanesulfonyl chloride2×HCID 760363,5-Dichloroanthranilic acidHCID 581589303-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 58158935HCID 58158935, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent5×

Procedure

To a 150 mL flask, methanesulfonyl chloride (1.1 g, 9.8 mmol), acetonitrile (20 mL) was added. Then the mixture of 3-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (3.0 g, 8.9 mmol, the product of step (3), example 4) and triethylamine (0.89 g, 8.9 mmol) in acetonitrile (30 mL) were added dropwise in 10 minutes at room temperature. The mixture was stirred for 1 hour. 2-Amino-3,5-dichlorobenzoic acid (1.6 g, 17 mmol) was added, and the reaction mixture turned into reddish brown. After being stirred for 30 minutes, the solution of triethylamine (1.8 g, 17 mmol) in acetonitrile (10 mL) was added dropwise and yellow solid precipitated. The mixture was stirred for 1 hour, another solution of methanesulfonyl chloride (1.1 g, 9.8 mmol) in acetonitrile (10 mL) was added. The reaction mixture turned into yellow and solid was precipitated. After being stirred for 1 hour, another solution of triethylamine (0.89 g, 8.9 mmol) in acetonitrile (4 mL) was added. Then the reaction mixture was stirred for overnight at room temperature. The reaction mixture was poured into water (100 mL), extracted with ethyl acetate (2×100 mL), washed with saturated sodium carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1/2) to give the product (2.0 g) as a yellow solid in 45% yield.

Workup

  1. stirringAfter being stirred for 30 minutes
  2. customyellow solid precipitated
  3. stirringThe mixture was stirred for 1 hour
  4. customwas precipitated
  5. stirringAfter being stirred for 1 hour
  6. stirringThen the reaction mixture was stirred for overnight at room temperature
  7. extractionextracted with ethyl acetate (2×100 mL)
  8. washwashed with saturated sodium carbonate solution and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1/2)

Sources & evidence

ORD record
ord-d9019fe8a40a4c0a92380b4b4b03f62c
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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