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

HRID 2262883Notes

Reaction equation

HRID 2262883 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.FC(F)(F)C(O)=O.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]([NH:31][C:32]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[O:33])=[N:23]1.C(N(CC)CC)C.O>CN(C)C=O>[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]([NH:31][C:32]([N:34]2[CH2:39][CH2:38][N:37]([C:2]3[S:6][N:5]=[C:4]([CH2:7][O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:3]=3)[CH2:36][CH2:35]2)=[O:33])=[N:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 542746325-Chloro-3-(phenoxymethyl)-1,2,4-thiadiazoleHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68777888N-1,2-Benzisoxazol-3-yl-4-[3-(phenoxymethyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-3-(phenoxymethyl)-1,2,4-thiadiazole (126 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 151 mg (61.7%) 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-3dd8b40eb2b742ebb766631e2d83d806
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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