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Dimethylformamide → 5-(1,1-Dioxo-1lambda6-iso-thiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazole

HRID 1619267
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1619267
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=O)=[O:26].[CH3:29][N:30](C=O)C>>[O:26]=[S:25]1(=[O:28])[CH2:24][CH2:23][CH2:22][N:30]1[CH2:29][C:16]1[CH:17]=[CH:18][C:12]2[S:11][C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]3)=[N:14][C:13]=2[CH:15]=1
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Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 1709623-chloropropane-1-sulfonic AcidHCID 106114582-(4-Isopropylpiperazin-1-yl)benzothiazole

Produkt 1

HCID 237289355-(1,1-Dioxo-1lambda6-iso-thiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazoleAusbeute 45 %

Versuchsvorschrift

To a solution of 5-aminomethyl-[2-(4-isopropylpiperazin-1-yl)benzothiazole (439 mg, 1.51 mmol) in DMF (10 mL) was added NaH (181 mg, 4.53 mmol) at 0° C. The mixture was allowed to warm to rt. After 30 min, a solution of 3-chloropropane-1-sulfonic acid (373 mg, 2.11 mmol) in DMF (1.67 mL) was added at rt. The reaction mixture was stirred at rt for 2 h and then quenched with water. The volatiles were removed and the residue was extracted with ethyl acetate. The organic extract was washed with brine and concentrated. The residue was purified by the preparative HPLC to give 267 mg (45%) of 5-(1,1-dioxo-1λ6-iso-thiazolidin-2-ylmethyl)-2-(4-isopropylpiperazin-1-yl)benzothiazole as a trifluoroacetate salt.

Aufarbeitung

  1. customquenched with water
  2. customThe volatiles were removed
  3. extractionthe residue was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. concentrationconcentrated
  7. customThe residue was purified by the preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2048a8db5059449da2ccda18b0ca5cc9
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772285B2

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