Ethanol → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1698077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698077
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15](OC)[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[NH2:19]CC1C=NC=CC=1.[CH2:27]([OH:29])C>O>[CH3:27][O:29][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([NH2:19])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 310183-PyridinemethanamineHCID 248037222-(6-Fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole

Produkt 1

HCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-(6-fluoropyridin-3-yl)-6-methoxy-1,3-benzothiazole (0.10 g, 0.38 mmol) and 3-(aminomethyl)pyridine (1.0 mL, 9.5 mmol) in ethanol (4 mL) was heated at 100° C. for 9 minutes in a microwave reactor. The mixture was diluted with water, then cooled to r.t. and the formed precipitate was collected by filtration and dried. The crude product was purified by prep. HPLC to give the title compound (71 mg) as a solid. 1H NMR (CHLOROFORM-d) δ 8.75 (d, 1H) 8.66 (d, 1H) 8.56 (dd, 1H) 8.11 (dd, 1H) 7.89 (d, 1H) 7.66-7.76 (m, 1H) 7.34 (d, 1H) 7.26-7.31 (m, 2H) 7.07 (dd, 1H) 6.50 (d, 1H) 5.18 (t, 1H) 4.67 (d, 2H) 3.90 (s, 3H); MS m/z (M+H) 348.9.

Aufarbeitung

  1. temperaturecooled to r.t.
  2. filtrationthe formed precipitate was collected by filtration
  3. customdried
  4. customThe crude product was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-409037e293694a51bae1d7e86cdffa6e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163928B2

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