Triethylamine → HCID 18982007, compound

HRID 1440783Notes

Reaction equation

HRID 1440783 reaction equation
[C:1]1([C:7]2[C:12](C(O)=O)=[CH:11][CH:10]=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C.[CH:46]([C:49]1[CH:55]=[CH:54][CH:53]=[C:52]([CH:56]([CH3:58])[CH3:57])[C:50]=1[NH2:51])([CH3:48])[CH3:47]>FC1C=CC=CC=1.O>[CH:56]([C:52]1[CH:53]=[CH:54][CH:55]=[C:49]([CH:46]([CH3:48])[CH3:47])[C:50]=1[NH:51][C:44]([NH:41][C:12]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:11]=1)=[O:29])([CH3:58])[CH3:57]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 18982012HCID 18982012, compound

Product 1

HCID 18982007HCID 18982007, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10008FluorobenzeneSolvent

Procedure

To a stirred mixture of 551 mg of 2,6-diphenyl-3-pyridinecarboxylic acid and 0.52 cc of diphenylphosphoryl azide in 6 cc of fluorobenzene was added dropwise 0.29 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and then heated at a temperature of 65°-70° C. for 10 minutes. After cooling, 0.45 cc of 2,6-diisopropylaniline was added and the resulting mixture was heated at a temperature of 70° C. for 1.5 hours. After cooling, water was added to the reaction mixture and extracted with chloroform. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: chloroform) to obtain 817 mg of compound 61.

Workup

  1. temperatureheated at a temperature of 65°-70° C. for 10 minutes
  2. temperatureAfter cooling
  3. temperaturethe resulting mixture was heated at a temperature of 70° C. for 1.5 hours
  4. temperatureAfter cooling
  5. extractionextracted with chloroform
  6. dry with materialThe extract was dried over magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe crude product thus obtained
  10. customwas purified by a silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-f5eca9916cc24f6f9007c595ed1b563b
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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