Water → N-1,2-Benzisoxazol-3-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide

HRID 2262885Notes

Reaction equation

HRID 2262885 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[N:3]=1.FC(F)(F)C(O)=O.[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([NH:28][C:29]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])=[N:20]1.C(N(CC)CC)C.O>CN(C)C=O>[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([NH:28][C:29]([N:31]2[CH2:36][CH2:35][N:34]([C:2]3[S:6][N:5]=[C:4]([C:7]4[S:8][CH:9]=[CH:10][CH:11]=4)[N:3]=3)[CH2:33][CH2:32]2)=[O:30])=[N:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27358235-Chloro-3-(2-thienyl)-1,2,4-thiadiazoleHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68780056N-1,2-Benzisoxazol-3-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamideYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-3-(2-thienyl)-1,2,4-thiadiazole (119 mg, 0.555 mmol) and N-1,2-benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate (200 mg, 0.555 mmol) in N,N-dimethylformamide (2 ml) was added triethylamine (0.389 ml, 2.78 mmol) at room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured to water, and the precipitated solid was separated by filtration, which was recrystallized from a mixed solvent of ethyl acetate and tetrahydrofuran to give 128 mg (55.9%) of the desired product.

Workup

  1. customthe precipitated solid was separated by filtration, which
  2. customwas recrystallized from a mixed solvent of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-13bd8a24a0e4440a9138b0ad3859ac02
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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