Diisopropylethylamine → HCID 11514839, Verbindung

HRID 2217331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217331
I.[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH2:14].Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.C(N(C(C)C)CC)(C)C>ClC(Cl)C>[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH:14][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 49796119HCID 49796119, Verbindung

Produkt 1

HCID 11514839HCID 11514839, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of 8H-Indeno[1,2-d]thiazol-2-ylamine hydroiodide 1a (Prepared in Example 1, Step 1, mg; mmol), nicotinoyl chloride hydrochloride (92 mg; 0.50 mmol) and diisopropylethylamine (0.50 mL; 2.77 mmol) in dichloroethane was heated in a sealed tube to 120° C. in a microwave oven for 10 minutes. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The residue was taken up into 2 M sodium carbonate solution and extracted with ethyl acetate. The extracts were dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was chromatographed on silica gel (eluent=50% ethyl acetate/hexanes to 100% ethyl acetate/hexanes gradient) to provide 43 mg of N-(8H-Indeno[1,2-d]thiazol-2-yl)-nicotinamide 7. EI-HRMS m/e calcd for C16H11N4OS (M+) 293.0623, found 293.0620.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customthe solvent removed in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed on silica gel (eluent=50% ethyl acetate/hexanes to 100% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2974063c7a2f4a8c90b33e077f51e383
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407977B2

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