Water → HCID 68779631, compound

HRID 2262893Notes

Reaction equation

HRID 2262893 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:18]=[C:17](Cl)[S:16][N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([NH:36][C:37]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[O:38])=[N:28]1.C(N(CC)CC)C.O>CN(C)C=O>[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([NH:36][C:37]([N:39]2[CH2:44][CH2:43][N:42]([C:17]3[S:16][N:15]=[C:14]([N:11]4[CH2:12][CH2:13][N:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH2:9][CH2:10]4)[N:18]=3)[CH2:41][CH2:40]2)=[O:38])=[N:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 687769531-(5-Chloro-1,2,4-thiadiazol-3-yl)-4-(phenylmethyl)piperazineHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68779631HCID 68779631, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyl-4-(5-chloro-1,2,4-thiadiazol-3-yl)piperazine (500 mg, 1.70 mmol) and N-1,2-benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate (612 mg, 1.70 mmol) in N,N-dimethylformamide (5 ml) was added triethylamine (1.18 ml, 8.50 mmol) at room temperature, and the mixture was stirred at room temperature for 0.5 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 recrystallized from a mixed solvent of ethyl acetate and hexane to give 347 mg (40.5%) of the desired product.

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 recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c25c09086720454186d7f9f9876783f4
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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