acetyl isothiocyanate

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:

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:

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: To a stirred solution of 3,4-diaminobenzophenone (8.48 g.; 0.04 mole) in ethyl ether (1.0 L.) there is added dropwise acetyl isothiocyanate (4.04 g.; 0.04 mole). The solution is stirred at room temperature for two hours and a precipitate collected by filtration and dried to afford 10.7 g. (85% yield) of 3-(3-acetylthioureido)-4-aminobenzophenone, m.p. 211° C., dec. a precipitate collected by filtration dried to afford 10.7 g

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

実験手順: To a suspension of 3-(3-carbomethoxythioureido)-4-aminobenzophenone (1.2 g.; 0.0036 mole) in acetone (15 ml.) is added acetyl isothiocyanate (0.37 g.; 0.0036 mole). The reaction mixture is heated to reflux and then allowed to stand at room temperature for 18 hours. The product is collected by filtration, washed successively to afford 0.85 g. (54% yield) of 3-(3-carbomethoxythioureido)-4-(3-acetylthioureido)benzophenone, m.p. 210° C., dec. The reaction mixture is heated to reflux The product is collected by filtration washed successively to afford 0.85 g

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

実験手順: A mixture of 2.69 g of 2-{2-[2-(4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl)ethyloxy]phenyl}thiazolidine, 0.78 g of acetyl isothiocyanate and 20 ml of acetone is stirred at room temperature for 2 hours. The reaction mixture is treated in the same manner as described in Example 73. 2.2 g of N-acetyl-2-{2-[2-(4-(3-fluorophenyl)-1,2,3,6-tetrahydropyridin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide are obtained. Yield: 65%. The reaction mixture is treated in the same manner

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

実験手順: Acetyl isothiocyanate (1.755 mL, 19.97 mmol) was added to a heated (100° C. oil bath) solution of cis-4-(5-amino-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)-N-isopropylcyclohexanecarbox-amide (8.06 g, 19.97 mmol) in dioxane (100 mL). After 5 minutes, complete conversion to the thiourea intermediate was observed. The reaction was cooled to RT, and EDC (11.49 g, 59.9 mmol) and DIPEA (12.56 mL, 71.9 mmol) were added. Heating was resumed at 60° C. for 2.5 hours. The reaction mixture was pre-absorbed onto silica gel, and purified via silica gel chromatography, eluting with 90:10:1 DCM:MeOH:NH4OH to yield cis-4-(2-acetamido-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-1-yl)-N-isopropylcyclohexanecarboxamide (8.56 g, 18.19 mmol, 91% yield) as an orange solid. MS m/z=471.2 [M+H], calc 470.61 for C25H38N6O3. Heating was resumed at 60° C. for 2.5 hours The reaction mixture was pre-absorbed onto silica gel purified via silica gel chromatography eluting with 90:10:1 DCM