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3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one
C27H41N3O4
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one; C27H41N3O4 With triethylamine In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 0 - 20℃; | 55.3% |
Stage #1: 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one; C27H41N3O4 With triethylamine In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 0 - 20℃; | 55.3% |
methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-(ethyl)amino)-2-methylbenzoate
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 3.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 4.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 5.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 6.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 6.2: 0 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: N,N-dimethyl-formamide / 0.33 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 3.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 4.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 5.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 6.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 6.2: 0 - 20 °C View Scheme |
methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 2.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 3.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 4.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 5.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 5.2: 0 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 2.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 3.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 4.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 5.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 5.2: 0 - 20 °C View Scheme |
methyl 5-bromo-3-(ethyl((trans)-4-(methylamino)cyclohexyl)amino)-2-methylbenzoate
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 2.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 3.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 4.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 4.2: 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 2.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 3.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 4.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 4.2: 0 - 20 °C View Scheme |
N-propargylmorpholine
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 2.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 3.2: 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 2.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 3.2: 0 - 20 °C View Scheme |
methyl 5-bromo-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methylbenzoate
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)ethynyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 2.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 3.2: 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 2.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 3.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 3.2: 0 - 20 °C View Scheme |
methyl 3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzoate
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / ethanol / 1 h / 60 °C 2.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 2.2: 0 - 20 °C View Scheme |
2-methyl-3-amino-5-bromobenzoic acid methyl ester
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: acetic acid / dichloromethane / 0.33 h / 20 °C 1.2: 16 h / 0 - 20 °C 2.1: acetic acid / dichloromethane / 0.33 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N,N-dimethyl-formamide / 0.33 h / 0 °C 3.2: 0 - 20 °C 4.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 5.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 7.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 8.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 8.2: 0 - 20 °C View Scheme |
N-(tert-butoxycarbonyl)-4-aminocyclohexanone
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: acetic acid / dichloromethane / 0.33 h / 20 °C 1.2: 16 h / 0 - 20 °C 2.1: acetic acid / dichloromethane / 0.33 h / 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N,N-dimethyl-formamide / 0.33 h / 0 °C 3.2: 0 - 20 °C 4.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 5.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 6.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 7.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 8.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 8.2: 0 - 20 °C View Scheme |
methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)amino)cyclohexyl)-amino)-2-methylbenzoate
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl((trans)-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)amino)-2-methyl-5-(3-morpholinoprop-1-yn-1-yl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: acetic acid / dichloromethane / 0.33 h / 20 °C 1.2: 16 h / 0 - 20 °C 2.1: N,N-dimethyl-formamide / 0.33 h / 0 °C 2.2: 0 - 20 °C 3.1: hydrogenchloride / methanol / 2 h / 0 - 20 °C 4.1: potassium carbonate; potassium iodide / acetonitrile / 16 h / 65 °C 5.1: triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 105 °C / Inert atmosphere 6.1: sodium hydroxide / water; ethanol / 1 h / 60 °C 7.1: triethylamine / dimethyl sulfoxide / 0.25 h / 20 °C 7.2: 0 - 20 °C View Scheme |
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