Triethylamine → HCID 68780873, compound

HRID 2262956Notes

Reaction equation

HRID 2262956 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](C(O)=O)=[CH:2]1.C([N:15]([CH2:18]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[C:37]1([C:43]2[N:47]=[C:46]([N:48]3[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]3)[S:45][N:44]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([NH:15][C:18]([N:51]2[CH2:52][CH2:53][N:48]([C:46]3[S:45][N:44]=[C:43]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:47]=3)[CH2:49][CH2:50]2)=[O:27])=[CH:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 69867Indole-3-Carboxylic AcidHCID 199401P,P-Diphenylphosphinic azideHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 68780873HCID 68780873, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of indole-3-carboxylic acid (162 mg, 1.00 mmol) and triethylamine (0.293 ml, 2.10 mmol) in toluene (10 ml) was added diphenylphosphoryl azide (0.226 ml, 1.05 mmol) at room temperature, and the mixture was stirred at room temperature for 30 minutes, followed by elevating the temperature to 90° C. and stirring for 1.5 hour. The resulting mixture was cooled to room temperature, 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (172 mg, 0.700 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 90 mg (27.3%) of the desired product as a solid.

Workup

  1. customto 90° C.
  2. stirringstirring for 1.5 hour
  3. temperatureThe resulting mixture was cooled to room temperature
  4. stirringthe mixture was stirred at room temperature for 3 hours
  5. extractionthe resulting solution was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  10. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-37ff0f340428499a9f737cf99a5bfddb
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…