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With trichlorophosphate; for 10.0h;Heating / reflux;
Step 2: 3,4,6- trichloropyridazine :A solution of 4-chloro-l,2-dihydropyridazine-3,6-dione in POCl3 (100 mL) was refluxed for10 h. The reaction mixture was concentrated and purified to yield 3,4,6-trichloropyridazine, which was used directly in the next step. M/Z 182.
A solution of 3,4,6-trichloropyridazine (20.0 g, 109.04 mmol) in HOAc (100 mL) was heated at 100 °C for 12 h, at which time TLC indicated the reaction had gone to completion. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (petroleum ether : Ethyl acetate = 1 : 1 ) to give the title compounds (11.2 g, 63percent yield) (1 : 1 ratio of regioisomers) as a white solid. LCMS M/Z (M+H) 165.
3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130 °C for two hours. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound.
3.7 g
With acetic acid; at 130.0℃; for 2.0h;
Example 18A 5,6-dichloropyridazin-3(2H)-one [0749] 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130° C. for two hours. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound.
3.7 g
With acetic acid; at 130.0℃; for 2.0h;
3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130 °C for two hours. After cooling to ambient temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound.
With sodium hydride; In tetrahydrofuran; at 20℃; for 16.0h;
EXAMPLE 55; 3-(l-(5-Ethylpyrimidin-2-yl)piperidin-4-yl)-N-(2-methyl-6-(methylsulfonyl) pyridin-3-yl)-[l,2,4]triazolo[4,3-b]pyridazin-8-amineStep 1: 3,6-Dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4- amine [0394] A 100-mL round-bottom flask was charged with a solution of 2-methyl- 6-(methylsulfonyl)pyridin-3-amine (500 mg, 2.69 mmol) in tetrahydrofuran (50 mL), sodium hydride (269 mg, 11.2 mmol), and 3,4,6-trichloropyridazine (1 g, 5.49 mmol). The resulting solution was stirred for 16 hrs at room temperature. The reaction was then quenched with brine (50 mL), extracted with ethyl acetate (4x50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a residue. This residue was purified by a silica gel column chromatography eluted with dichloromethane/ethyl acetate (2/1) affording 3,6-dichloro-N-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)pyridazin-4-amine as pale yellow solid (0.75 g, 84%).
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