6-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamide → HCID 178485216, Verbindung

HRID 1484451

Reaktionsgleichung

Reaktionsgleichung von HRID 1484451
CS[C:3]([N:6]1[N:10]=[CH:9][C:8]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:7]1)=[N:4][CH3:5].[Cl:16][C:17]1[N:18]=[C:19]2[N:23]([C:24]=1[S:25]([NH2:28])(=[O:27])=[O:26])[CH:22]=[CH:21][S:20]2>C(#N)C>[CH3:5][NH:4][C:3]([N:6]1[N:10]=[CH:9][C:8]2([CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH2:7]1)=[N:28][S:25]([C:24]1[N:23]2[C:19]([S:20][CH:21]=[CH:22]2)=[N:18][C:17]=1[Cl:16])(=[O:27])=[O:26]

Komponenten

4

Edukt 2

HCID 27798396-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamideHCID 67360788N-methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl ester

Produkt 1

HCID 178485216HCID 178485216, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

0.42 g (1 mol equiv.) N-Methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl ester and 0.46 g (1.05 mol equiv.) 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid amide were added to 7 mL acetonitrile and the reaction mixture was refluxed overnight. Volatiles were removed under reduced pressure, and the residue was taken up in ethylacetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (EtOAc) afforded 0.56 g (69%) 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid methylamino-(8-oxa-2,3-diaza-spiro[4.5]dec-3-en-2-yl)-methylene-amide. 1H NMR (400 MHz, CDCl3) δ 1.51-1.57 (m, 2H), 1.80-1.89 (m, 2H), 3.10 (d, J=5.0 Hz, 3H), 3.51-3.59 (m, 2H), 3.83-3.90 (m, 4H), 3.89 (s, 2H), 6.89 (s, 1H), 6.99 (d, J=4.6 Hz, 1H), 7.12 (br.s., 1H), 8.01 (d, J=4.6 Hz, 1H).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight
  2. customVolatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-efd19343a54c46ca985cd9c28e61078d
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422244B2

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