Triethylamine → HCID 68777868, compound

HRID 2263034Notes

Reaction equation

HRID 2263034 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:25][C:26]1[C:30]([N:31]=[C:32]=[O:33])=[C:29]([CH3:34])[O:28][N:27]=1>O1CCCC1>[CH3:25][C:26]1[C:30]([NH:31][C:32]([N:15]2[CH2:16][CH2:17][N:12]([C:10]3[S:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:11]=3)[CH2:13][CH2:14]2)=[O:33])=[C:29]([CH3:34])[O:28][N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 68777868HCID 68777868, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.812 mmol) and triethylamine (0.113 ml, 0.812 mmol) in tetrahydrofuran (2.5 ml) was added 3,5-dimethylisoxazol-4-yl isocyanate (168 mg, 1.22 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. 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 ethyl acetate to give 214 mg (68.6%) of the desired product as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  3. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-83f1902e259c4893835d41fe128879f7
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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