Triethylamine → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine

HRID 1183413Notes

Reaction equation

HRID 1183413 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.[CH2:17]([N:19](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:41]([NH:49][NH2:50])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.O(Cl)Cl.[P+5]>C1(C)C=CC=CC=1.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH:19][C:17]2[O:48][C:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[N:49][N:50]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11955BenzoylhydrazineHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acidHCID 178479711HCID 178479711, compound

Product 1

HCID 66577739[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-(5-phenyl-[1,3,4]oxadiazol-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (1 g, 3.6 mmol), triethylamine (1 mL, 7.2 mmol) and diphenylphosphoryl azide (1.98 g, 7.2 mmol) were placed in toluene (20 mL) and heated to 60° C. for 20 minutes. Benzoic acid hydrazide (0.98 g, 7.2 mmol) was added in a single portion and the reaction was heated and stirred for 2 hours. The reaction was cooled and submitted to aqueous workup. The crude material was dissolved in dioxane (100 mL), phosphorous(V) oxychloride was added and the reaction was heated to 100° C. overnight. The reaction was cooled and worked up and the residue was purified on silica gel (0-80% EtOAc in hexanes) to yield the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureThe reaction was cooled
  3. temperaturethe reaction was heated to 100° C. overnight
  4. temperatureThe reaction was cooled
  5. customthe residue was purified on silica gel (0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-df8f2e5bc4e84add93f82b7458bd1572
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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