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

HRID 2262947Notes

Reaction equation

HRID 2262947 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][O:26][C:27]1[CH:28]=[C:29]([N:35]=[C:36]=[O:37])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]>O1CCCC1>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([NH:35][C:36]([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:37])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 35178104-Isocyanato-1,2-dimethoxybenzene

Product 1

HCID 68778676N-(3,4-dimethoxyphenyl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideYield 18.7%

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 3,4-dimethoxyphenyl isocyanate (0.182 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, and the residue was recrystallized from tetrahydrofuran to give 64.6 mg (18.7%) of the desired product as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-1b66dd1e84304a79b57e04776c9bd5bf
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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