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

HRID 2263006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263006
Cl[C:2]1[S:6][N:5]=[C:4]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]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]([N:7]4[CH2:11][CH2:10][CH2:9][CH2:8]4)[N:3]=3)[CH2:33][CH2:32]2)=[O:30])=[N:20]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 652686795-Chloro-3-(pyrrolidin-1-yl)-1,2,4-thiadiazoleHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

Produkt 1

HCID 68778591N-1,2-Benzisoxazol-3-yl-4-(3-pyrrolidin-1-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-3-pyrrolidin-1-yl-1,2,4-thiadiazole (158 mg, 0.833 mmol) and N-1,2-benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate (300 mg, 0.833 mmol) in N,N-dimethylformamide (3 ml) was added triethylamine (0.581 ml, 4.17 mmol) at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. 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 hexane and ethyl acetate to give 28.5 mg (8.58%) of the desired product.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-130fbb7ddafe4e868e57e5f62ff1c8df
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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