Water → HCID 68780025, compound

HRID 2262888Notes

Reaction equation

HRID 2262888 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH: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]([C:7]4[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=4)[N:3]=3)[CH2:34][CH2:33]2)=[O:31])=[N:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 21928608HCID 21928608, compoundHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Product 1

HCID 68780025HCID 68780025, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-chloro-1,2,4-thiadiazol-3-yl)pyridine (104 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 50.0 mg (22.1%) 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-60f3e3f14de64a0fa7af81eaf7f645db
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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