Octahydropyrrolo[3,4-c]pyrrole derivative and application method and application thereof
A technology for drugs and compounds, applied in the field of drugs, can solve problems such as safety rejection of approval, and achieve the effects of high safety, good metabolic stability, and good bioavailability
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Embodiment 1
[0168] Example 1: (5-(1,6-phthalazin-5-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(5-methyl-2-( Synthesis of 2H-1,2,3-triazol-2-yl)phenyl)methanone
[0169]
[0170] Step 1) Synthesis of 5-chloro-1,6-naphthalene
[0171] Add 1,6-naphthyridine-5(6H)-one (3.00g, 20.53mmol) and phosphorus oxychloride (40mL) into a 100mL reaction flask, and heat the reaction to 100°C for 24 hours. The reaction was stopped, the reaction solution was cooled to room temperature, and excess phosphorus oxychloride was distilled off under reduced pressure. The remaining solid was quenched with ice saturated sodium bicarbonate solution (80 mL), and the aqueous phase was extracted with dichloromethane (30 mL×3). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried under reduced pressure and purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v)=1 / 1) to obtain the title compound (white solid, 3.08g, 91.20%).
[017...
Embodiment 2
[0194] Example 2: (5-(1,6-phthalazin-5-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-(2H-1,2 , Synthesis of 3-triazol-2-yl)phenyl)methanone
[0195]
[0196] Step 1) Synthesis of 2-(2H-1,2,3-triazol-2-yl)benzoic acid
[0197] The title compound of this step was prepared by referring to the method described in step 4 of Example 1, that is, 2H-1,2,3-triazole (0.7g, 10.08mmol), 2-iodobenzoic acid (1g, 4.03mmol), carbonic acid Cesium (2.36g, 7.2mmol), trans-N,N'-dimethyl-1,2-cyclohexanediamine (0.103g, 0.752mmol) and cuprous iodide (0.077g, 0.403mmol) on N , prepared by reaction in N-dimethylformamide (18mL), the crude product was separated and purified by silica gel column chromatography (dichloromethane / methanol (v / v)=30 / 1) to obtain the title compound (yellow solid, 0.511g, 67%).
[0198] MS(ESI,neg.ion)m / z:188.1[M-H] - ;
[0199] 1 H NMR (DMSO-d 6 ,600MHz)δ(ppm):13.06(s,1H),8.08(s,2H),7.78~7.75(m,2H),7.72~7.68(m,1H),7.60~7.57(m,1H);
[0200] 13 C NMR (DMSO-d 6 ,1...
Embodiment 3
[0208] Example 3: (5-(1,6-phthalazin-5-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-fluoro-6-(2H Synthesis of -1,2,3-triazol-2-yl)phenyl)methanone
[0209]
[0210] Step 1) Synthesis of 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid
[0211] The title compound of this step was prepared by referring to the method described in step 4 of Example 1, that is, 2H-1,2,3-triazole (6.9g, 100mmol), 2-fluoro-6-iodobenzoic acid (10.64g, 40mmol ), cesium carbonate (23.4g, 71.7mmol), trans-N,N'-dimethyl-1,2-cyclohexanediamine (1.02g, 7.04mmol) and cuprous iodide (0.76g, 4.0mmol ) in N,N-dimethylformamide (50mL), the crude product was separated and purified by silica gel column chromatography (dichloromethane / methanol (v / v)=50 / 1) to obtain the title compound (yellow solid, 5.62g, 67.90%).
[0212] MS(ESI,pos.ion)m / z:208.10[M+H] +
[0213] 1 H NMR (DMSO-d 6 ,400MHz)δ(ppm):13.66(s,1H),8.16(s,2H),7.79(d,J=8.2Hz,1H),7.68(td,J=8.2,6.2Hz,1H),7.44( t,J=8.8Hz,1H).
[0214] Step 2) Sy...
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