Triethylamine → HCID 178522631, compound

HRID 2095200Notes

Reaction equation

HRID 2095200 reaction equation
[C:1]1([C:7]2[C:8](=[N:13][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([NH2:12])=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([C:7]2[C:8](=[N:13][NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:9]([NH:12][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=3)=[N:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 178509135HCID 178509135, compound

Product 1

HCID 178522631HCID 178522631, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Phenyl-4-(phenylhydrazono)-4H-pyrazol-3-ylamine (66 mg, 0.25 mmol) was dissolved in 5 mL of anhydrous methylene chloride. Nicotinoylchloride hydrochloride (50 mg, 0.28 mmol) and triethylamine (78 μL, 0.56 mmol) were added to the solution. Slight fuming of the reaction was noted and the solution became red. The reaction was stirred at ambient temperature for 48 hours. The reaction was filtered to remove a small amount of white solid. To the filtrate was added 30 mL of methylene chloride. The solution was washed with 20 mL of a 5% HCl solution. The aqueous layer was washed with methylene chloride and the combined methylene chloride fractions were washed with water and saturated NaHCO3 solution. The methylene chloride solution was dried over MgSO4, filtered, and evaporated to afford a solid. The material was purified by flash chromatography (CH2Cl2:MeOH=15:1) to yield 34 mg (36%) of the title compound as a yellow solid. 1H NMR (ppm, 200 MHz, CDCl3) δ 7.30-7.55 (m, 8H), 7.75 (d, 2H), 8.20-8.30 (m, 2H), 8.55 (d, 1H), 8.81 (d, 1H), 9.45 (s, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. customto remove a small amount of white solid
  3. additionTo the filtrate was added 30 mL of methylene chloride
  4. washThe solution was washed with 20 mL of a 5% HCl solution
  5. washThe aqueous layer was washed with methylene chloride
  6. washthe combined methylene chloride fractions were washed with water and saturated NaHCO3 solution
  7. dry with materialThe methylene chloride solution was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto afford a solid
  11. customThe material was purified by flash chromatography (CH2Cl2:MeOH=15:1)

Sources & evidence

ORD record
ord-fc6f7d38e1344756b0d2d3087982dd17
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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