Toluene → HCID 10954464, Verbindung

HRID 1798993

Reaktionsgleichung

Reaktionsgleichung von HRID 1798993
[CH3:1][C@:2]12[C:11](=O)[O:10][C:8](=[O:9])[C@@:7]1([CH3:13])[C@H:6]1[O:14][C@@H:3]2[CH2:4][CH2:5]1.[NH2:15]C1SC2C=C(C(O)=O)C=CC=2N=1.C1(C)C=CC=CC=1>C(N(CC)CC)C>[CH3:1][C@:2]12[C:11](=[O:10])[NH:15][C:8](=[O:9])[C@@:7]1([CH3:13])[C@H:6]1[O:14][C@@H:3]2[CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 5944CantharidinHCID 667406-Benzothiazolecarboxylic acid, 2-amino-

Produkt 1

HCID 10954464HCID 10954464, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of cantharidin (50 mg, 0.26 mmol), 2-amino-6-carboxybenzothiazole (294 mg, 1.27 mmol), and a mixture of dried toluene and dried triethylamine (4 mL; 2:1, v/v) may be sealed in a tube and heated for 3 hours at 180° C. The reaction mixture may be concentrated, followed by flash chromatography (dichloromethane:methanol, 10:1) that may give the product CAN039 (51.9 mg, 55%) of formula (3) as a white solid with the following characterization: mp=180-181° C.; Rf=0.27 (hexane:acetone, 2:1); 1H NMR (CD3OD, 500 MHz): δ 1.34 (6H, s), 1.72-1.74 (2H, m), 1.97-2.00 (2H, m), 4.69-4.70 (2H, m), 8.08 (1H, d, J=8.5 Hz), 8.18 (1H, dd, J=8.5 Hz and 1.5 Hz), 8.70-8.71 (1H, m); 13C NMR (CDCl3): δ 12.1, 23.7, 54.6, 85.0, 85.1, 122.5, 123.9, 127.9, 128.3, 132.7, 151.9, 155.3, 168.0, 178.7; MS (EI) m/z (%): 372 (M+); HRMS calcd. for C18H16N2O5S [M]+ found 358.0776.

Aufarbeitung

  1. custom2:1, v/v) may be sealed in a tube
  2. concentrationThe reaction mixture may be concentrated

Quellen und Nachweise

ORD-Eintrag
ord-227a8410acca40029fa41b2f65c6de9f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344007B2

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