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CAS No. : | 1342815-16-0 | MDL No. : | MFCD28502287 |
Formula : | C19H27ClN6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 406.91 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | N/A | |
Precautionary Statements: | UN#: | N/A | |
Hazard Statements: | Packing Group: | N/A |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | (0163) 4-Amino-5-chloro-2-methoxybenzoic acid (0.20 g) was dissolved in dichloromethane (10 mL) and cooled to C. N-methyl morpholine (0.12 g) and isobutyl chloroformate (0.16 g) were sequentially added to the solution and stirred for 3 hours. A reaction solution was prepared by sequentially adding triethylamine (0.20 g) and [1-{3-(1H-1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methanamine hydrochloride (0.31 g) thereto. The temperature of the reaction solution was elevated and the solution was stirred under reflux. After 4 hours of stirring, water (10 mL) was added thereto, stirred for 5 minutes and a layer was separated. Dichloromethane (10 mL) was added to an aqueous layer and an organic layer was extracted. Water (10 mL) and 1N hydrochloric acid (3 mL) were added to the collected organic layers to extract the aqueous layer. 1N sodium hydroxide (4 mL) was added to the aqueous layer, and the extraction was performed twice with a mixed solvent of dichloromethane (8 mL) and 2-propanol (2 mL). The collected organic layers were dried with sodium sulfate and filtered, and then washed with dichloromethane (10 mL). The solvent was removed by concentrating the filtered organic solution under reduced pressure. The resulting solids were dried under reduced pressure at 19-22 C. for 18 hours to obtain the titled compound (0.39 g; yield: 98%). (0164) 1H NMR (400 MHz, CDCl3) delta 8.08 (s, 1H), 7.72 (m, 1H), 7.66 (s, 1H), 7.54 (s, 1H), 6.27 (s, 1H), 4.43 (t, 2H), 4.36 (s, 1H), 3.88 (s, 3H), 3.30 (t, 2H), 2.83 (d, 2H), 2.27 (t, 2H), 2.06 (t, 2H), 1.90 (t, 2H), 1.70 (m, 2H), 1.58 (m, 1H), 1.29 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | (0173) 4-Amino-5-chloro-2-methoxybenzoic acid (0.20 g) was dissolved in acetonitrile (10 mL). Carbonyldiimidazole (0.19 g) was added to the solution and stirred at 19-22 C. for 4 hours. After triethylamine (0.20 g) and [1-{3-(1H-1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methanamine (0.27 g) were sequentially added thereto, the temperature of the resulting solution was elevated. Then the solution was stirred under reflux. After 21 hours of stirring, water (10 mL) was added thereto, stirred for 5 minutes, and layers were separated. Dichloromethane (10 mL) was added to an aqueous layer and an organic layer was extracted. Water (10 mL) and 1N hydrochloric acid (4 mL) were added to the collected organic layers to extract the aqueous layer. 2N sodium hydroxide (about 4 mL) was added to the aqueous layer to adjust pH of about 10. The extraction was performed twice with a mixed solvent of dichloromethane (8 mL) and 2-propanol (2 mL). The collected organic layers were dried with anhydrous magnesium sulfate and filtered, and then washed with dichloromethane (10 mL). The solvent was removed by concentrating the filtered organic solution under reduced pressure. The resulting solids were dried under reduced pressure at 19-22 C. for 17 hours to obtain the titled compound (0.41 g; yield: 100%). (0174) 1H NMR (400 MHz, CDCl3) delta 8.08 (s, 1H), 7.72 (m, 1H), 7.66 (s, 1H), 7.54 (s, 1H), 6.27 (s, 1H), 4.43 (t, 2H), 4.36 (s, 1H), 3.88 (s, 3H), 3.30 (t, 2H), 2.83 (d, 2H), 2.27 (t, 2H), 2.06 (t, 2H), 1.90 (t, 2H), 1.70 (m, 2H), 1.58 (m, 1H), 1.29 (m, 2H) | |
100% | 4-Amino-5-chloro-2-methoxybenzoic acid (0.20 g) was dissolved in acetonitrile (10 mL). Carbonyldiimidazole (0.19 g) was added to the solution and stirred at 19-22 C. for 4 hours. After triethylamine (0.20 g) and [1-{3-(1H-1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methanamine (0.27 g) were sequentially added thereto, the temperature of the resulting solution was elevated. Then the solution was stirred under reflux. After 21 hours of stirring, water (10 mL) was added thereto, stirred for 5 minutes, and layers were separated. Dichloromethane (10 mL) was added to an aqueous layer and an organic layer was extracted. Water (10 mL) and 1N hydrochloric acid (4 mL) were added to the collected organic layers to extract the aqueous layer. 2N sodium hydroxide (about 4 mL) was added to the aqueous layer to adjust pH of about 10. The extraction was performed twice with a mixed solvent of dichloromethane (8 mL) and 2-propanol (2 mL). The collected organic layers were dried with anhydrous magnesium sulfate and filtered, and then washed with dichloromethane (10 mL). The solvent was removed by concentrating the filtered organic solution under reduced pressure. The resulting solids were dried under reduced pressure at 19-22 C. for 17 hours to obtain the titled compound (0.41 g; yield: 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium iodide; calcium carbonate / acetonitrile / 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 50 °C / 7500.75 Torr 3.1: 1,1'-carbonyldiimidazole / acetonitrile / 4 h / 19 - 22 °C 3.2: 21 h / Reflux | ||
Multi-step reaction with 4 steps 1.1: potassium iodide; calcium carbonate / acetonitrile / 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 50 °C / 7500.75 Torr 3.1: ethanol / 4 h 4.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 3 h / Cooling 4.2: 14 h / Reflux | ||
Multi-step reaction with 4 steps 1.1: potassium iodide; calcium carbonate / acetonitrile / 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 50 °C / 7500.75 Torr 3.1: diethyl ether; ethanol / 4 h 4.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 3 h / Cooling 4.2: 14 h / Reflux |
Multi-step reaction with 4 steps 1.1: potassium iodide; calcium carbonate / acetonitrile / 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 50 °C / 7500.75 Torr 3.1: acetone / 4 h 4.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 3 h / Cooling 4.2: 14 h / Reflux | ||
Multi-step reaction with 4 steps 1.1: potassium iodide; calcium carbonate / acetonitrile / 16 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / methanol / 18 h / 50 °C / 7500.75 Torr 3.1: acetone / 4 h 4.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 3 h / Cooling 4.2: 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | (0165) 4-Amino-5-chloro-2-methoxybenzoic acid (0.2 g) was dissolved in dichloromethane (10 mL) and cooled to C. N-methyl morpholine (0.12 g) and isobutyl chloroformate (0.16 g) were sequentially added to the solution and stirred for 3 hours. A reaction solution was prepared by sequentially adding triethylamine (0.2 g) and [1-{3-(1H-1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methanamine oxalate (0.37 g) thereto, and the temperature of the reaction solution was elevated. The reaction solution was stirred under reflux. After 4 hours of stirring, water (10 ml) was added thereto, stirred for 5 minutes, and layers were separated. Dichloromethane (10 mL) was added to an aqueous layer and an organic layer was extracted. Water (10 mL) and 1N hydrochloric acid (3 mL) were added to the collected organic layers to extract the aqueous layer. 1N sodium hydroxide (4 mL) was added to the aqueous layer and the extraction was performed twice with a mixed solvent of dichloromethane (8 mL) and 2-propanol (2 mL). The collected organic layers were dried with sodium sulfate and filtered, and then washed with dichloromethane (10 mL). The solvent was removed by concentrating the filtered organic solution under reduced pressure. The resulting solids were dried under reduced pressure at 19-22 C. for 18 hours to obtain the titled compound (0.36 g; yield: 90%). (0166) 1H NMR (400 MHz, CDCl3) delta 8.08 (s, 1H), 7.72 (m, 1H), 7.66 (s, 1H), 7.54 (s, 1H), 6.27 (s, 1H), 4.43 (t, 2H), 4.36 (s, 1H), 3.88 (s, 3H), 3.30 (t, 2H), 2.83 (d, 2H), 2.27 (t, 2H), 2.06 (t, 2H), 1.90 (t, 2H), 1.70 (m, 2H), 1.58 (m, 1H), 1.29 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | (0169) 4-Amino-5-chloro-2-methoxybenzoic acid (0.20 g) was dissolved in dichloromethane (10 mL) and cooled to C. N-methyl morpholine (0.12 g) and isobutyl chloroformate (0.16 g) were sequentially added to the solution and stirred for 3 hours. A reaction solution was prepared by sequentially adding triethylamine (0.20 g) and [1-{3-(1H-1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methanamine succinate (0.41 g) thereto. The temperature of the reaction solution was elevated and the stirring was performed under reflux. After 14 hours of stirring, water (10 mL) was added thereto, stirred for 5 minutes and layers were separated. Dichloromethane (10 mL) was added to an aqueous layer and an organic layer was extracted. Water (10 mL) and 1N hydrochloric acid (3 mL) were added to the collected organic layers to extract the aqueous layer. 1N sodium hydroxide (4 mL) was added to the aqueous layer and the extraction was performed twice with a mixed solvent of dichloromethane (8 mL) and 2-propanol (2 mL). The collected organic layers were dried with sodium sulfate and filtered, and then washed with dichloromethane (10 mL). The solvent was removed by concentrating the filtered organic solution under reduced pressure. The resulting solids were dried under reduced pressure at 19-22 C. for 18 hours to obtain the titled compound (0.36 g; yield: 90%). (0170) 1H NMR (400 MHz, CDCl3) delta 8.08 (s, 1H), 7.72 (m, 1H), 7.66 (s, 1H), 7.54 (s, 1H), 6.27 (s, 1H), 4.43 (t, 2H), 4.36 (s, 1H), 3.88 (s, 3H), 3.30 (t, 2H), 2.83 (d, 2H), 2.27 (t, 2H), 2.06 (t, 2H), 1.90 (t, 2H), 1.70 (m, 2H), 1.58 (m, 1H), 1.29 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | (0167) 4-Amino-5-chloro-2-methoxybenzoic acid (0.20 g) was dissolved in dichloromethane (10 mL) and cooled to C. N-methyl morpholine (0.12 g) and isobutyl chloroformate (0.16 g) were sequentially added to the solution and stirred for 3 hours. A reaction solution was prepared by sequentially adding triethylamine (0.20 g) and [1-{3-(1H-1,2,3-triazol-1-yl)propyl}piperidin-4-yl]methanamine citrate (0.49 g) thereto. The temperature of the reaction solution was elevated and the reaction solution was stirred under reflux. After 14 hours of stirring, water (10 mL) was added thereto, stirred for 5 minutes and layers were separated. Dichloromethane (10 mL) was added to an aqueous layer and an organic layer was extracted. Water (10 mL) and 1N hydrochloric acid (3 mL) were added to the collected organic layers to extract the aqueous layer. 1N sodium hydroxide (4 mL) was added to the aqueous layer and the extraction was performed twice with a mixed solvent of dichloromethane (8 mL) and 2-propanol (2 mL). The collected organic layers were dried with sodium sulfate and filtered, and then washed with dichloromethane (10 mL). The solvent was removed by concentrating the filtered organic solution under reduced pressure. The resulting solids were dried under reduced pressure at 19-22 C. for 18 hours to obtain the titled compound (0.35 g; yield: 88%). (0168) 1H NMR (400 MHz, CDCl3) delta 8.08 (s, 1H), 7.72 (m, 1H), 7.66 (s, 1H), 7.54 (s, 1H), 6.27 (s, 1H), 4.43 (t, 2H), 4.36 (s, 1H), 3.88 (s, 3H), 3.30 (t, 2H), 2.83 (d, 2H), 2.27 (t, 2H), 2.06 (t, 2H), 1.90 (t, 2H), 1.70 (m, 2H), 1.58 (m, 1H), 1.29 (m, 2H) |