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CAS 112101-81-2
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide
Codes: Tamsulosin Hydrochloride-019
Application context (from source-drug indications)
Erectile dysfunctionTadalafil/TamsulosinBenign prostatic hyperplasiaTadalafil/TamsulosinLower urinary tract symptomsSolifenacin Succinate/Tamsulosin HydrochlorideBenign prostatic hyperplasiaSolifenacin Succinate/Tamsulosin HydrochlorideOveractive bladderSolifenacin Succinate/Tamsulosin HydrochlorideDrug-related adverse effects and reactionsSolifenacin Succinate/Tamsulosin HydrochlorideBladder neck obstructionSolifenacin Succinate/Tamsulosin HydrochlorideBenign prostatic hyperplasiaDutasteride/Tamsulosin HydrochlorideBenign prostatic hyperplasiaTamsulosin HydrochlorideUrinary tract infectionTamsulosin HydrochlorideUrinary retentionTamsulosin HydrochlorideInguinal herniaTamsulosin HydrochlorideVoiding dysfunctionTamsulosin HydrochlorideLower urinary tract symptomsTamsulosin Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Tadalafil/Tamsulosin | Tier C — Watch / trade | - |
| Solifenacin Succinate/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Dutasteride/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
2-(2-Ethoxyphenoxy)ethanol→2-(2-Ethoxyphenoxy)ethyl mesylate→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 4total yield: 18g(Tamsulosin Hydrochloride (API))
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 2total yield: 20.4g(Tamsulosin (Free))
2-(2-Ethoxyphenoxy)ethanol→2-(2-Ethoxyphenoxy)ethyl mesylate→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 14total yield: 2.091g(Tamsulosin Hydrochloride (API))
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 5total yield: 46.28gTamsulosin Hydrochloride (API)
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 4total yield: 18g(Tamsulosin Hydrochloride (API))
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
2-(2-Ethoxyphenoxy)ethanol→2-(2-Ethoxyphenoxy)ethyl mesylate→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 14total yield: 2.091g(Tamsulosin Hydrochloride (API))
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 5total yield: 46.28gTamsulosin Hydrochloride (API)
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→Benzaldehyde→4-Methoxybenzaldehyde→4-Formylphenol→(4-Fluorophenyl)methanone→2-methoxy-5-[(2R)-2-[(E)-(phenylmethylidene)amino]propyl]benzene-1-sulfonamide→2-Methoxy-5-[(2R)-2-[(E)-[(4-methoxyphenyl)methylidene]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Hydroxyphenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→5-[(2R)-2-[(E)-[(4-Fluorophenyl)methylidene]amino]propyl]-2-methoxybenzene-1-sulfonamide→1-ethoxy-2-(2-iodoethoxy)benzene→(E)-[2-(2-ethoxyphenoxy)ethyl][(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl](phenylmethylidene)azanium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-methoxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-hydroxyphenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(2R)-N-[2-(2-Ethoxyphenoxy)ethyl]-N-[(E)-(4-fluorophenyl)methylidene]-1-(4-methoxy-3-sulfamoylphenyl)propan-2-iminium iodide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
2-(2-Ethoxyphenoxy)ethanol→2-(2-Ethoxyphenoxy)ethyl mesylate→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide
(-)-alpha-Amino-p-hydroxyhydrocinnamic acid→N-Acetyl-L-tyrosine→Ethyl N-acetyl-L-tyrosinate→Ethyl N-acetyl-O-methyl-L-tyrosinate→N-[(2S)-1-Hydroxy-3-(4-methoxyphenyl)propan-2-yl]acetamide→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→1-Methoxy-4-[(1E)-2-nitroprop-1-en-1-yl]benzene→N-Hydroxy-1-(4-methoxyphenyl)propan-2-imine→N-[(1E)-1-(4-Methoxyphenyl)prop-1-en-2-yl]acetamide→N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl 4-methylbenzenesulfonate→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-Hydroxy-2-ethoxybenzene→1-Chloro-2-hydroxyethane→2-(2-Ethoxyphenoxy)ethanol
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
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