Triethylamine → 4-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-3-thienylpiperazine-1-carboxamide

HRID 2262948Notes

Reaction equation

HRID 2262948 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.[S:25]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26]1>O1CCCC1>[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:31]([NH:30][C:27]4[CH:28]=[CH:29][S:25][CH:26]=4)=[O:32])[CH2:14][CH2:13]3)[S:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27763803-IsocyanatothiopheneHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 687798084-(3-Phenyl-1,2,4-thiadiazol-5-yl)-N-3-thienylpiperazine-1-carboxamideYield 16.6%

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 ml) was added 3-thienyl isocyanate (0.152 ml, 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 50.0 mg (16.6%) of the desired product.

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-69da68bda7c24f70aa6e195b173e4096
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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