Reaktion #62042

Reaktionsgleichung

5-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylamino]-3-hydroxy-isothiazole-4-carbonitrile

DL-2-amino-1-propanol

→

desired product

5-[4-(2,5-Dichloro-phenoxy)-3-fluoro-phenylamino]-3-hydroxy-N-(2-hydroxy-1-methyl-ethyl)-isothiazole-4-carboxamidine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed in a high-pressure reaction equipment
2. 2
   TemperaturThe reaction mixture was cooled to room temperature
3. 3
   Sonstigethe solvent was removed in vacuo
4. 4
   SonstigeThe residue was chromatographed by silica gel column (chloroform/methanol, 25:1)

Vorschrift

A mixture of 5-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylamino]-3-hydroxy-isothiazole-4-carbonitrile (0.2 g) and DL-2-amino-1-propanol (0.7 g) in 20 ml of ethanol was placed in a high-pressure reaction equipment and heated to 100° C. overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was chromatographed by silica gel column (chloroform/methanol, 25:1) to give the desired product as a light yellow solid. MS: 470; 1H NMR (DMSO-d6, 300 MHz): δ 10.60 (brs, 1/2H, NH, D2O exchangeable), 9.69 (brs, 1/2H, NH, D2O exchangeable), 9.22 (brs, 1/2H, NH, D2O exchangeable), 8.55 (s, 1H, OH, D2O exchangeable), 7.91 (brs, 1/2H, NH, D2O exchangeable), 7.70 (brs, 1/2H, NH, D2O exchangeable), 7.61 (d, 1H, J=8.7 Hz, ArH), 7.22 (dd, 1H, J=2.1, 8.7 Hz, ArH), 7.16 (t, 1H, J=8.7 Hz, ArH), 6.99 (dd, 1H, J=2.1, 12.6 Hz, ArH), 6.88 (d, 1H, J=2.1 Hz, ArH), 6.83 (dd, 1H, J=2.1, 8.7 Hz, ArH), 5.09 (brs, 1H, OH), 3.80 (m, 1H, CH), 3.49 (m, 1H, CH). 3.44 (m, 1H, CH), 1.15 (d, 3H, J=6.3 Hz, CH3).

Quelle