Category: 1201676-03-0

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.03, as common compound, the synthetic route is as follows.Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-lH,2H,3H-pyrrolo[3,4-c]pyridin-l-one (200 mg, 1.0 mmol, 1 eq), bromo(cyclopropyl)zinc (5.9 mL of 0.5M solution in THF, 2.7 mmol, 3 eq), palladium (II) acetate (22 mg, 0.1 mmol, 0.1 eq), 2′-(dicyclohexylphosphanyl)-N2,N2,N6,N6-tetramethyl-[l,r- biphenyl] -2,6-diamine (86 mg, 0.2 mmol, 0.2 eq) and THF (2 mL) was heated at 65 – 75 C for 18 h. After cooling to rt, the reaction was subject to aqueous work-up and chromatography on silica gel to afford 91 mg of the title compound as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.03, as common compound, the synthetic route is as follows.Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-lH,2H,3H-pyrrolo[3,4-c]pyridin-l-one (200 mg, 1.0 mmol, 1 eq), bromo(cyclopropyl)zinc (5.9 mL of 0.5M solution in THF, 2.7 mmol, 3 eq), palladium (II) acetate (22 mg, 0.1 mmol, 0.1 eq), 2′-(dicyclohexylphosphanyl)-N2,N2,N6,N6-tetramethyl-[l,r- biphenyl] -2,6-diamine (86 mg, 0.2 mmol, 0.2 eq) and THF (2 mL) was heated at 65 – 75 C for 18 h. After cooling to rt, the reaction was subject to aqueous work-up and chromatography on silica gel to afford 91 mg of the title compound as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1201676-03-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.03, as common compound, the synthetic route is as follows.

A solution of 4,6-dichloro-2H,3H-pyrrolo[3,4-c]pyridin-l-one (1.0 g, 4.9 mmol, 1 eq.), 2- cyclopropyl-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (2.0 mL, 11 mmol, 2.2 eq.), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (0.80 g, 1.0 mmol, 0.2 eq.) and potassium carbonate (3.4 g, 25 mmol, 5 eq.) in dioxane-water (10: 1 v/v, 15 mL) was degassed and heated at 80 C for 16 hours. After cooling the mixture, it was diluted with water and extracted with 15% isopropanol in chloroform (3x). The combined organic layers were dried, filtered and concentrated. The product was purified chromatography B to afford the title compound (0.44 g, 42%) as a white solid.

Statistics shows that 1201676-03-0 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (1.19 g, 5.87 mmol), triethylamine (2.97 g, 29.3 mmol), and crude trifluoroacetic acid salt of piperidine-4- carboxylic acid isobutyl amide [obtained by stirring 4-isobutylcarbamoyl-piperidine-1- carboxylic acid te/f-butyl ester (2.63 g, 8.80 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (6 mL) for 1.5 hours, then removing solvents by rotary evaporation] in dioxane (10 mL) is heated in a 75 mL sealed tube at 120 0C for 68 h. Filtration of room temperature mixture does not lead to separation of regioisomers. The filtrate is concentrated down to dryness by rotary evaporation, dissolved into ethyl acetate, and then washed with water and brine. The organic layer is dried over sodium sulfate, filtered and concentrated down to dryness by rotary evaporation. This residue is then combined with solids from first filtration and eluted through a silica gel column (80:20 ethyl acetate / heptane, then 100% ethyl acetate, then 95:5 ethyl acetate / methanol). The more polar regioisomer (TLC solvents: 90:10 ethyl acetate / methanol) is concentrated down to dryness by rotary evaporation, then treated with a small amount of methanol. The pink solid is isolated by filtration (0.647 g, 1.84 mmol, 31 %). MS(ESI) m/z 351.20 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.00 (s, 1 H), 7.79 (t, J=5.81 Hz, 1 H), 6.84 (s, 1 H), 4.54 (s, 2 H), 4.19 (d, J=13.39 Hz, 2 H), 3.09 – 2.92 (m, 2 H), 2.86 (dd, J=6.57, 6.06 Hz, 2 H), 2.48 – 2.36 (m, 1 H), 1.79 – 1.71 (m, 2 H), 1.71 – 1.52 (m, 3 H), 0.82 (d, J=6.82 Hz, 6 H).

The synthetic route of 1201676-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (1.19 g, 5.87 mmol), triethylamine (2.97 g, 29.3 mmol), and crude trifluoroacetic acid salt of piperidine-4- carboxylic acid isobutyl amide [obtained by stirring 4-isobutylcarbamoyl-piperidine-1- carboxylic acid te/f-butyl ester (2.63 g, 8.80 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (6 mL) for 1.5 hours, then removing solvents by rotary evaporation] in dioxane (10 mL) is heated in a 75 mL sealed tube at 120 0C for 68 h. Filtration of room temperature mixture does not lead to separation of regioisomers. The filtrate is concentrated down to dryness by rotary evaporation, dissolved into ethyl acetate, and then washed with water and brine. The organic layer is dried over sodium sulfate, filtered and concentrated down to dryness by rotary evaporation. This residue is then combined with solids from first filtration and eluted through a silica gel column (80:20 ethyl acetate / heptane, then 100% ethyl acetate, then 95:5 ethyl acetate / methanol). The more polar regioisomer (TLC solvents: 90:10 ethyl acetate / methanol) is concentrated down to dryness by rotary evaporation, then treated with a small amount of methanol. The pink solid is isolated by filtration (0.647 g, 1.84 mmol, 31 %). MS(ESI) m/z 351.20 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.00 (s, 1 H), 7.79 (t, J=5.81 Hz, 1 H), 6.84 (s, 1 H), 4.54 (s, 2 H), 4.19 (d, J=13.39 Hz, 2 H), 3.09 – 2.92 (m, 2 H), 2.86 (dd, J=6.57, 6.06 Hz, 2 H), 2.48 – 2.36 (m, 1 H), 1.79 – 1.71 (m, 2 H), 1.71 – 1.52 (m, 3 H), 0.82 (d, J=6.82 Hz, 6 H).

The synthetic route of 1201676-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

4,6-Dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (5.63 g, 27.7 mmol), te/f-butyl piperazine-1-carboxylate (7.75 g, 41.6 mmol), triethylamine (14.Og, 139 mmol), and dioxane (50 ml.) are stirred at 120 0C in a 350 ml. sealed tube for 16 h. To the cooled down reaction mixture are then added more te/f-butyl piperazine-1-carboxylate (5.2 g, 27.7 mmol) and triethylamine (2.83 g, 28.0 mmol). The vessel is sealed again and stirred at 120 0C for 24 h. The reaction mixture is then cooled to ambient temperature, and a light-pink solid is isolated by filtration (6.18 g, 17.5 mmol, 63%). MS(ESI) m/z 353.15 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.04 (s, 1 H), 6.89 (s, 1 H), 4.57 (s, 2 H), 3.61 – 3.54 (m, 4 H), 3.47 – 3.41 (m, 4 H), 1.42 (s, 9 H).D. 4-(4-Chloro-1 -oxo-2,3-dihydro-1 H-pyrrolo[3,4-c]pyridin-6-yl)-piperazine-1 -carboxylic acid terf-butyl ester. The title compound is typically obtained from the dioxane filtrate after isolation of 4- (6-chloro-1 -oxo-2,3-dihydro-1 /-/-pyrrolo[3,4-c]pyridin-4-yl)-piperazine-1 -carboxylic acid tert- butyl ester. The dioxane is removed by rotary evaporation. Treatment with methanol yields a light yellow solid which is isolated by filtration. MS(ESI) m/z 353.30 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 8.93 (s, 1 H), 7.01 (s, 1 H), 4.28 (s, 2 H), 3.58 – 3.53 (m, 4 H), 3.45 – 3.40 (m, 4 H), 1.42 (S, 9 H).

With the rapid development of chemical substances, we look forward to future research findings about 1201676-03-0.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

4,6-Dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (5.63 g, 27.7 mmol), te/f-butyl piperazine-1-carboxylate (7.75 g, 41.6 mmol), triethylamine (14.Og, 139 mmol), and dioxane (50 ml.) are stirred at 120 0C in a 350 ml. sealed tube for 16 h. To the cooled down reaction mixture are then added more te/f-butyl piperazine-1-carboxylate (5.2 g, 27.7 mmol) and triethylamine (2.83 g, 28.0 mmol). The vessel is sealed again and stirred at 120 0C for 24 h. The reaction mixture is then cooled to ambient temperature, and a light-pink solid is isolated by filtration (6.18 g, 17.5 mmol, 63%). MS(ESI) m/z 353.15 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.04 (s, 1 H), 6.89 (s, 1 H), 4.57 (s, 2 H), 3.61 – 3.54 (m, 4 H), 3.47 – 3.41 (m, 4 H), 1.42 (s, 9 H).D. 4-(4-Chloro-1 -oxo-2,3-dihydro-1 H-pyrrolo[3,4-c]pyridin-6-yl)-piperazine-1 -carboxylic acid terf-butyl ester. The title compound is typically obtained from the dioxane filtrate after isolation of 4- (6-chloro-1 -oxo-2,3-dihydro-1 /-/-pyrrolo[3,4-c]pyridin-4-yl)-piperazine-1 -carboxylic acid tert- butyl ester. The dioxane is removed by rotary evaporation. Treatment with methanol yields a light yellow solid which is isolated by filtration. MS(ESI) m/z 353.30 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 8.93 (s, 1 H), 7.01 (s, 1 H), 4.28 (s, 2 H), 3.58 – 3.53 (m, 4 H), 3.45 – 3.40 (m, 4 H), 1.42 (S, 9 H).

With the rapid development of chemical substances, we look forward to future research findings about 1201676-03-0.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1201676-03-0 ,Some common heterocyclic compound, 1201676-03-0, molecular formula is C7H4Cl2N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (0.655 g, 3.23 mmol), triethylamine (2.61 g, 25.8 mmol), and 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3- a]pyrazine hydrochloride (0.544 g, 3.39 mmol) in dioxane (7.5 ml.) is stirred in a 48 ml_ sealed tube at 12O0C for 16 h. Additional 5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3-a]pyrazine hydrochloride (0.500 g, 3.11 mmol) is added to the mixture, which is heated again at 12O0C for 24 h. A light yellow powder is isolated by filtration of the room temperature reaction mixture (0.61 1 g, 2.10 mmol, 65%). MS(ESI) m/z 291.18 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.1 1 (s, 1 H), 8.50 (s, 1 H), 7.01 (s, 1 H), 4.97 (s, 2 H), 4.68 (s, 2 H), 4.19 (t, J=5.31 Hz, 2 H), 4.01 (t, J=5.43 Hz, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1201676-03-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem