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

HRID 2262892Notes

Reaction equation

HRID 2262892 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:3]=1.FC(F)(F)C(O)=O.[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:22]([NH:29][C:30]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[O:31])=[N:21]1.C(N(CC)CC)C.O>CN(C)C=O>[O:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:22]([NH:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([C:2]3[S:6][N:5]=[C:4]([N:7]4[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]4)[N:3]=3)[CH2:34][CH2:33]2)=[O:31])=[N:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 652671425-Chloro-3-(piperidin-1-yl)-1,2,4-thiadiazoleHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68780043N-1,2-Benzisoxazol-3-yl-4-(3-piperidin-1-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-chloro-1,2,4-thiadiazol-3-yl)piperidine (114 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 1 hour. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1) to give the desired product as a solid. The resulting solid was recrystallized from a mixed solvent of ethyl acetate, tetrahydrofuran and hexane to yield 44.0 mg (10.7%) of the desired product. mp 214-215° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-37e811c482b04b59a56c69d3c01ca9b2
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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