Triethylamine → HCID 68778006, compound

HRID 2262941Notes

Reaction equation

HRID 2262941 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.[C:25]([C:27]1[CH:28]=[C:29]([N:33]=[C:34]=[O:35])[CH:30]=[CH:31][CH:32]=1)#[N:26]>O1CCCC1>[C:25]([C:27]1[CH:28]=[C:29]([NH:33][C:34]([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:35])[CH:30]=[CH:31][CH:32]=1)#[N:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333153-IsocyanatobenzonitrileHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 68778006HCID 68778006, compoundYield 64.4%

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 ml) was added 3-cyanophenyl isocyanate (176 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 high performance liquid chromatography (YMC HPLC Column eluted with 10% to 100% Liquid A; Liquid A: a 0.1% solution of trifluoroacetic acid in acetonitrile; Liquid B: an aqueous 0.1% trifluoroacetic acid solution) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 204 mg (64.4%) of the desired product as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe residue was purified by high performance liquid chromatography (YMC HPLC Column
  3. washeluted with 10% to 100% Liquid A
  4. customLiquid B: an aqueous 0.1% trifluoroacetic acid solution) and recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-6ae54ec8b4df4c5c83c63cdab097a6bb
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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