反応 #62041

反応方程式

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

isopropylamine

→

desired product

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

溶媒

ethanol

反応条件

後処理

1. 1
   その他was placed into a high-pressure reaction apparatus
2. 2
   温度The reaction mixture was cooled to room temperature
3. 3
   その他the solvent was removed in vacuo
4. 4
   その他The residue was chromatographed by silica gel column (chloroform/methanol, 40:1)

実験手順

A mixture of 5-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylamino]-3-hydroxy-isothiazole-4-carbonitrile (0.2 g) and isopropylamine (5 ml) in 20 ml of ethanol was placed into a high-pressure reaction apparatus 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, 40:1) to give the desired product as a light yellow solid. MS: 454; 1H NMR (DMSO-d6, 300 MHz): δ 10.28 (brs, 1/2H, NH, D2O exchangeable), 9.62 (brs, 1H, NH, D2O exchangeable), 9.31 (brs, 1/2H, NH, D2O exchangeable), 8.57 (s, 1H, OH, D2O exchangeable), 7.88 (brs, 1H, 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), 3.85 (m, 1H, CH), 1.20 (d, 6H, J=6.3 Hz, 2×CH3).

出典