Triazolopyrazinones as PDE1 inhibitors
A technology of triazolo and pyrazine, which is applied in the field of triazolopyrazinone as a PDE1 inhibitor, and can solve problems such as not disclosing it
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no. 1 example E1
[0031] In a first embodiment E1, the invention relates to a compound (compound I) of formula (I):
[0032]
[0033] Compound (I)
[0034] in
[0035] n is 0 or 1;
[0036] R 1 selected from the group consisting of: linear or branched C 1 -C 8 Alkyl, such as C 1 to C 3 Alkyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl and saturated monocyclic C 3 -C 8 Cycloalkyl; or
[0037] R 1 selected from the group consisting of oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, saturated monocyclic C 3 -C 8 Cycloalkyl, and substituted by fluorine one or more times, preferably once, twice or three times, straight or branched chain C 1 -C 8 alkyl; and
[0038] R 2 selected from the group consisting of: linear or branched C 1 -C 8 Alkyl, phenyl, saturated monocyclic C 3 -C 8 Cycloalkyl, saturated bicyclic C 4 -C 10 Cycloalkyl, saturated tricyclic C 7 -C 10 Cycloalkyl, oxetanyl, tetrahydrofuranyl and tetrahydropyranyl; or
[0039] R 2 is selected from the group con...
example 1
[0175] Intermediate 1:
[0176]
[0177] 3-Propyl-[1,2,4]triazolo[4,3-a]pyrazin-8(7H)-one:
[0178] To a solution of commercially available 2-chloro-3-hydrazinopyrazine (28 g, 0.19 mol) in dichloromethane (200 mL) was added butyraldehyde (14.7 g, 0.20 mol) and the reaction was allowed to cool before cooling to 0 °C. Stir at 50°C for 2 hours. Diacetoxyiodobenzene (71.8 g, 0.223 mol) was added at 0°C. The cooling was removed and the mixture was stirred at 20 °C for 2 hours. Na 2 CO 3 (80 mL) of saturated aqueous solution was slowly poured into the reaction, and the mixture was stirred for 10 min. The organic phase was separated, washed with brine (3×50 mL), washed with Na 2 SO 4 Dry and concentrate under vacuum. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate and petroleum ether to give 8-chloro-3-propyl-[1,2,4]triazolo[4,3-a]pyridine Azine 20 g (53%).
[0179] Dioxane (120mL) and H 2 A mixture of 8-chloro-3-propyl-[...
example 2
[0181]
[0182] 3-Propyl-7-((tetrahydro-2H-pyran-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyrazine-8(7H)- ketone:
[0183] Step 1: To a solution of (tetrahydro-2H-pyran-3-yl)methanol (300 mg, 2.58 mmol) and TEA (522 mg, 5.17 mmol) in dichloromethane (10 mL) was added methanesulfonate at 0 °C Acid chloride (355 mg, 3.10 mmol) and the reaction was allowed to warm to 20°C and stir for 1 hour. The solution was washed with saturated NaHCO 3 Aqueous solution (2mL), H 2 O (3 x 2 mL), washed with brine (1 mL), dried and concentrated to give (tetrahydro-2H-pyran-3-yl)methyl mesylate (500 mg), which was used directly in the next step .
[0184] Step 2: Dissolve (tetrahydro-2H-pyran-3-yl)methyl mesylate (500 mg, 2.58 mmol) and 3-propyl-[1,2,4]triazole in DMF (30 mL) And[4,3-a]pyrazin-8(7H)-one (413mg, 2.32mmol) was added K 2 CO 3 (534 mg, 3.87 mmol). The mixture was stirred at 60°C for 4 hours. The reaction was cooled to RT and diluted with DCM (100 mL). Wash the organic phase wit...
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