Triethylamine → N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2262954Notes

Reaction equation

HRID 2262954 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.[N:25]([C:28]1[CH:37]=[CH:36][C:31]2[O:32][CH2:33][CH2:34][O:35][C:30]=2[CH:29]=1)=[C:26]=[O:27]>O1CCCC1>[O:32]1[C:31]2[CH:36]=[CH:37][C:28]([NH:25][C:26]([N:15]3[CH2:16][CH2:17][N:12]([C:10]4[S:9][N:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:11]=4)[CH2:13][CH2:14]3)=[O:27])=[CH:29][C:30]=2[O:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27761726-Isocyanato-2,3-dihydro-1,4-benzodioxineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazine

Product 1

HCID 68780082N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 46.9%

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 6-isocyanato-1,4-benzodioxan (167 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 161 mg (46.9%) 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-206c316ed22e4f4f9ea24f9583002d4f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…