2,2-diethylbutanedioic acid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3.5 g (20 mol) of 2,2-diethylsuccinic acid and 10 ml of acetyl chloride was heated under reflux for 2 hr, cooled, concentrated in vacuo, and reconcentrated three times after the addition of toluene. The residue was used without further purification. was heated under reflux for 2 hr cooled concentrated in vacuo after the addition of toluene The residue was used without further purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 9.26 g (53 mmol) of 2,2-diethylsuccinic acid and 30 ml of acetyl chloride was heated under reflux for 1.5 hr, cooled, and concentrated in vacuo. The residue was reconcentrated twice with toluene and then dissolved in 150 ml of 1,2-dimethoxyethane. To this solution was added 7.56 g (26.4 mmol) of the (E)-3-[2-[4-(cyclohexyl)-2-thiazolyl]-ethenyl]benzeneamine and 10.9 g of sodium acetate dissolved in 150 ml of 1,2-dimethoxyethane. This reaction mixture was heated on the steam bath for 3.5 hr and then concentrated in vacuo. The residue was digested with 600 ml of water on the steam bath for 20 min. The solid was collected to give 10 g of crude product. Recrystallization from ethanol gave 3.5 g of product, mp 180°-185°. Further recrystallization from methanol gave (E)-4-[[3-[2-(4-cyclohexyl-2-thiazolyl)-ethenyl]phenyl]amino]-2-methylene-4-oxobutanoic acid as off-white needles, mp 187°-189°. was heated under reflux for 1.5 hr cooled concentrated in vacuo dissolved in 150 ml of 1,2-dimethoxyethane This reaction mixture was heated on the steam bath for 3.5 hr concentrated in vacuo The solid was collected to give 10 g of crude product Recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3.5 g (20 mol) of 2,2-diethylsuccinic acid and 10 ml of acetyl chloride was heated under reflux for 2 hr, cooled, concentrated in vacuo, and reconcentrated three times after the addition of toluene. The residue was used without further purification. was heated under reflux for 2 hr cooled concentrated in vacuo after the addition of toluene The residue was used without further purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3.5 g (20 mol) of 2,2-diethylsuccinic acid and 10 ml of acetyl chloride was heated under reflux for 2 hr, cooled, concentrated in vacuo, and reconcentrated three times after the addition of toluene. The residue was used without further purification. was heated under reflux for 2 hr cooled concentrated in vacuo after the addition of toluene The residue was used without further purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 9.26 g (53 mmol) of 2,2-diethylsuccinic acid and 30 ml of acetyl chloride was heated under reflux for 1.5 hr, cooled, and concentrated in vacuo. The residue was reconcentrated twice with toluene and then dissolved in 150 ml of 1,2-dimethoxyethane. To this solution was added 7.56 g (26.4 mmol) of the (E)-3-[2-[4-(cyclohexyl)-2-thiazolyl]-ethenyl]benzeneamine and 10.9 g of sodium acetate dissolved in 150 ml of 1,2-dimethoxyethane. This reaction mixture was heated on the steam bath for 3.5 hr and then concentrated in vacuo. The residue was digested with 600 ml of water on the steam bath for 20 min. The solid was collected to give 10 g of crude product. Recrystallization from ethanol gave 3.5 g of product, mp 180°-185°. Further recrystallization from methanol gave (E)-4-[[3-[2-(4-cyclohexyl-2-thiazolyl)-ethenyl]phenyl]amino]-2-methylene-4-oxobutanoic acid as off-white needles, mp 187°-189°. was heated under reflux for 1.5 hr cooled concentrated in vacuo dissolved in 150 ml of 1,2-dimethoxyethane This reaction mixture was heated on the steam bath for 3.5 hr concentrated in vacuo The solid was collected to give 10 g of crude product Recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 9.26 g (53 mmol) of 2,2-diethylsuccinic acid and 30 ml of acetyl chloride was heated under reflux for 1.5 hr, cooled, and concentrated in vacuo. The residue was reconcentrated twice with toluene and then dissolved in 150 ml of 1,2-dimethoxyethane. To this solution was added 7.56 g (26.4 mmol) of the (E)-3-[2-[4-(cyclohexyl)-2-thiazolyl]-ethenyl]benzeneamine and 10.9 g of sodium acetate dissolved in 150 ml of 1,2-dimethoxyethane. This reaction mixture was heated on the steam bath for 3.5 hr and then concentrated in vacuo. The residue was digested with 600 ml of water on the steam bath for 20 min. The solid was collected to give 10 g of crude product. Recrystallization from ethanol gave 3.5 g of product, mp 180°-185°. Further recrystallization from methanol gave (E)-4-[[3-[2-(4-cyclohexyl-2-thiazolyl)-ethenyl]phenyl]amino]-2-methylene-4-oxobutanoic acid as off-white needles, mp 187°-189°. was heated under reflux for 1.5 hr cooled concentrated in vacuo dissolved in 150 ml of 1,2-dimethoxyethane This reaction mixture was heated on the steam bath for 3.5 hr concentrated in vacuo The solid was collected to give 10 g of crude product Recrystallization from ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Analogously to Example 3, the title compound is prepared starting from 3-(7-benzyloxy-2-quinolinylmethoxy)aniline and 2,2-diethylsuccinic acid. Slightly yellowish crystals of m.p. 89°-95° are obtained; IR (KBr): 3325, 2966, 1689, 1599, 1545, 1512, 1492, 1436, 1380, 1208, 1157, 1024, 842, 775, 695 cm-1. Slightly yellowish crystals of m.p. 89°-95° are obtained

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Analogously to Example 3, the title compound is prepared from 2,2-diethylsuccinic acid and 3-(6,7-difluoro-2-quinolinylmethoxy)aniline. It is obtained in the form of a white solid; 1H-NMR, 200 MHz, DMSO, delta (ppm)=9.90 (s, 1H), 8.42 (d, 1H), 8.10 (m, 2H), 7.70 (d, 1H), 7.45 (m, 1H), 7.07 (m, 2H), 6.73 (d, 1H), 5.35 (s, 2H), 2.58 (s, 2H), 1.80 (m, 4H), 0.80 (t, 6H). It is obtained in the form of a white solid