112101-81-2

Usage

Uses

Used in Cancer Treatment:
R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide is used as an inhibitor of carbonic anhydrase IX for its potential to suppress tumor growth and metastasis in various cancers. Its selectivity for the overexpressed enzyme in cancer cells makes it a promising candidate for targeted cancer therapy.
Used in Hypoxic Tumor Treatment:
R-MAB-203 is used as a therapeutic agent for hypoxic tumors, which are resistant to traditional chemotherapy and radiation therapy. Its ability to inhibit carbonic anhydrase IX may help overcome the resistance of these tumors to conventional treatments.
Used in Pharmaceutical Industry:
R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide is used as a research compound in the pharmaceutical industry for the development of new cancer treatments. Its potential applications in cancer therapy and other medical fields are currently being explored through ongoing research.

InChI:InChI=1/C10H13NO4S/c1-7(12)5-8-3-4-9(15-2)10(6-8)16(11,13)14/h3-4,6H,5H2,1-2H3,(H2,11,13,14)

Synthetic route

(R)-2-(N-(trifluoroacetyl)arnino)-1-(4'-methoxy-3'-sulphamoyl)-phenylpropane (842130-16-9) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With water; potassium carbonate In methanol for 8h; Heating / reflux;	89%

(4R,5S)-5-(4-methoxy-3-sulfamoylphenyl)-4-methyloxazolidin-2-one (957777-99-0) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 1h; atmospheric pressure;	87%

C10H16N2O3S*C10H16O4S (906338-31-6) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With ammonia In water at 0 - 25℃; for 1h; pH=9.89 - 10.18; Product distribution / selectivity;	82.06%

(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With potassium carbonate In water Product distribution / selectivity;	82%

(R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide (112101-74-3) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Stage #1: (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide With hydrogenchloride; water for 16 - 18h; Heating / reflux; Stage #2: With sodium carbonate In water for 0.5h; pH=~ 10; Product distribution / selectivity;	80%
Stage #1: (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide With hydrogenchloride; water for 18h; Heating / reflux; Stage #2: With potassium carbonate In water Product distribution / selectivity;	80%

5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride (116091-64-6) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Stage #1: 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybensulfonamide hydrochloride; pyrographite In methanol at 20℃; for 0.5h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol at 60 - 65℃; under 2942.29 - 3677.86 Torr; Stage #3: With ammonia In water	80%

(R)-5-(2-azidopropyl)-2-methoxybenzenesulfonamide (937018-25-2) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 1h;

(S)-5-(2-hydroxypropyl)-2-methoxybenzenesulfonamide (937018-24-1) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / pyridine / 2 h / 20 °C 2: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 3: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl acetate (937018-23-0) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / KOH / methanol 2: 88 percent / pyridine / 2 h / 20 °C 3: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 4: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(S)-1-(3-(chlorosulfonyl)-4-methoxyphenyl)propan-2-yl acetate (937018-21-8) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 2: 91 percent / KOH / methanol 3: 88 percent / pyridine / 2 h / 20 °C 4: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 5: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl methanesulfonate → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 2: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(S)-(+)-1-(4-methoxyphenyl)propan-2-ol (131029-01-1) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: 90 percent / pyridine 2: 85 percent / chlorosulfonic acid / 1 h / 0 °C 3: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 4: 91 percent / KOH / methanol 5: 88 percent / pyridine / 2 h / 20 °C 6: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 7: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(S)-1-(4-methoxyphenyl)propan-2-yl acetate (131029-02-2) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 85 percent / chlorosulfonic acid / 1 h / 0 °C 2: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 3: 91 percent / KOH / methanol 4: 88 percent / pyridine / 2 h / 20 °C 5: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 6: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

4-methoxy-benzaldehyde (123-11-5) + indenyl magnesium bromide → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions

Yield

Multi-step reaction with 9 steps 1: 21 percent / glucose / baker's yeast / H2O / 72 h / 20 °C 2: 86 percent / H2; HClO4 / Pd/C / ethanol / 20 °C / atmospheric pressure 3: 90 percent / pyridine 4: 85 percent / chlorosulfonic acid / 1 h / 0 °C 5: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 6: 91 percent / KOH / methanol 7: 88 percent / pyridine / 2 h / 20 °C 8: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 9: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(1R,2S)-1-(4'-methoxyphenyl)-1,2-propanediol (111004-04-7) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions

Yield

Multi-step reaction with 8 steps 1: 86 percent / H2; HClO4 / Pd/C / ethanol / 20 °C / atmospheric pressure 2: 90 percent / pyridine 3: 85 percent / chlorosulfonic acid / 1 h / 0 °C 4: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 5: 91 percent / KOH / methanol 6: 88 percent / pyridine / 2 h / 20 °C 7: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 8: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme

(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide D-tartrate (863666-27-7) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 1h; pH=9.5 - 10;
With sodium hydroxide In water at 20℃; for 1h; pH=9.5 - 10;
With sodium hydroxide In water at 25 - 30℃; for 1h; pH=9.5 - 10.0;	n/a

(+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (112244-38-9) → (S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide (119714-13-5) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With optical-resolution agent; diethylamine In methanol; ethanol at 40℃; Purification / work up; Optical-resolution column;	A n/a B n/a

(R)(+)-N-acetyl-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
In hydrogenchloride

(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide dibenzoyl-D-tartrate (1161025-56-4) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With potassium carbonate In water at 20℃; for 1h;	8 g

5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate (1210430-94-6) → 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With potassium carbonate In water at 20℃; for 3h;	0.45 g
With hydrogenchloride In water; isopropyl alcohol at 45 - 50℃; for 1h; pH=2 - 3;

2-methoxy-5-(2-oxopropyl)benzenesulfonamide (116091-63-5) → (S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide (119714-13-5) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / methanol / 5 h / 20 °C 2: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 20 °C / 2206.72 Torr View Scheme

2-methoxy-5-(2-hydroxyiminopropyl)benzenesulfonamide (944395-49-7) → (S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide (119714-13-5) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In methanol at 20℃; under 2206.72 Torr; for 8h;

N-benzenesulfonyl-N,N-bis(2-chloroethyl)amine (58023-19-1) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → 2-methoxy-5-{(2R)-2-[4-(benzenelsulfonyl)piperazin-1-yl]propyl}benzenesulfonamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 125 - 130℃; for 10h;	90.83%

bromoacetic acid (79-08-3) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

Conditions	Yield
Stage #1: bromoacetic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -45 - -40℃; for 4h; Stage #2: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide In dichloromethane at -45 - -40℃; for 1.5h; Product distribution / selectivity;	89.2%

(R)-10-camphorsulfonic acid (35963-20-3) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → C10H16N2O3S*C10H16O4S (906338-31-6)

Conditions	Yield
In water; isopropyl alcohol at 0 - 4℃; for 1.5h; Product distribution / selectivity; Heating / reflux;	85.65%

2-Bromoacetyl bromide (598-21-0) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; Product distribution / selectivity;	80%

methyl 2-ethoxyphenoxyacetate + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide (133261-17-3)

Conditions	Yield
Stage #1: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With diisobutylaluminium hydride In tetrahydrofuran at 0 - 25℃; for 1.08333h; Stage #2: methyl 2-ethoxyphenoxyacetate In tetrahydrofuran; toluene at 20 - 25℃; for 16h;	77%

2-(2-ethyloxyphenoxy)ethyl methanesulfonate (169506-15-4) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (R)-tamsulosin (106133-20-4)

Conditions	Yield
With potassium hydrogencarbonate; potassium iodide In acetonitrile at 80℃; for 24h;	74%

1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (160969-00-6) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide (1031281-18-1)

Conditions	Yield
In isopropyl alcohol for 16h; Reflux;	69%

2-(o-ethoxyphenoxy)-ethyl bromide + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → 5-((R)-2-{bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide (918867-88-6)

Conditions	Yield
With sodium oxalate In N,N-dimethyl-formamide at 80℃;	64%

2-(2-ethyloxyphenoxy)ethyl methanesulfonate (169506-15-4) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → tamsulosin hydrochloride (106133-20-4)

Conditions	Yield
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With sodium hydrogencarbonate; potassium iodide In DMF (N,N-dimethyl-formamide) at 55 - 65℃; for 11h; Stage #2: With hydrogenchloride In ethanol pH=2;	56.9%
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With calcium oxide In 2-methyl-propan-1-ol at 80 - 85℃; for 25h; Stage #2: With hydrogenchloride In 2-methyl-propan-1-ol; water at 60 - 65℃; pH=1.0; Product distribution / selectivity;
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With calcium oxide In ethanol at 78 - 80℃; for 35h; Stage #2: With hydrogenchloride In ethanol; water at 60 - 65℃; pH=1.0; Product distribution / selectivity;
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With calcium oxide In 2-methyl-propan-1-ol at 80 - 85℃; for 25h; Stage #2: With hydrogenchloride In 2-methyl-propan-1-ol; water at 60 - 65℃; pH=1.0; Product distribution / selectivity;

2-(o-ethoxyphenoxy)-ethyl bromide + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (R)-tamsulosin (106133-20-4)

Conditions	Yield
With sodium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; for 5h;	50%
Stage #1: 2-(o-ethoxyphenoxy)-ethyl bromide; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide In methanol at 25 - 35℃; for 48h; Heating / reflux; Stage #2: With potassium carbonate In dichloromethane; water
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 1.5h; Product distribution / selectivity;

1-(2-bromoethoxy)-2-isopropoxybenzene (1262059-05-1) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (-)-5-((2R)-2-{[2-(2-isopropoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide (1262059-02-8)

Conditions	Yield
In i-Amyl alcohol for 3h; Reflux;	37%

2-(o-ethoxyphenoxy)-ethyl bromide + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → tamsulosin hydrochloride (106133-20-4)

Conditions	Yield
In ethanol Heating / reflux;	32%
Stage #1: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With sodium hydrogencarbonate In triethyl phosphite Stage #2: 2-(o-ethoxyphenoxy)-ethyl bromide In water; triethyl phosphite for 6h; Heating / reflux; Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;	30.36%
In ethanol for 16h; Heating / reflux;

1-(benzyloxy)-2-(2-bromoethoxy)benzene (154582-47-5) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (-)-5-[(2R)-2-({2-[2-(benzyloxy)phenoxy]ethyl}amino)propyl]-2-methoxybenzenesulfonamide (1262059-03-9)

Conditions	Yield
In i-Amyl alcohol for 3h; Reflux;	25%

2-[2-(2,2,2-trifluoroethoxy)-phenoxy]ethyl 4-methylbenzenesulfonate (459868-80-5) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → (-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide (1031281-18-1)

Conditions	Yield
In i-Amyl alcohol for 3h; Reflux;	4%

2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → 5-[(R)-2-(4-Amino-6,7-dimethoxy-quinazolin-2-ylamino)-propyl]-2-methoxy-benzenesulfonamide

Conditions	Yield
In i-Amyl alcohol for 5h; Heating;

2-(2-ethoxyphenoxy)acetaldehyde (103181-55-1) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → 5-{2-[2-(2-ethoxy-phenoxy)-ethylideneamino]-propyl}-2-methoxy-benzenesulfonamide

Conditions	Yield
In ethanol at 20℃; for 1h;

Upstream product

• 86225-65-2 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride 
• 116091-64-6 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride 
• 1161025-56-4 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide dibenzoyl-D-tartrate 
• 116091-63-5 2-methoxy-5-(2-oxopropyl)benzenesulfonamide 
• 944395-49-7 5-(2-hydroxyiminopropyl)-2-methoxybenzenesulfonamide 
• 1210430-94-6 5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate 
• 957777-99-0 (4R,5S)-5-(4-methoxy-3-sulfamoylphenyl)-4-methyloxazolidin-2-one 
• 906338-31-6 C₁₀H₁₆N₂O₃S*C₁₀H₁₆O₄S 
• 112244-38-9 (+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide 
• 112101-74-3 (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide 
• 863666-27-7 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide D-tartrate 
• 111004-04-7 (1R,2S)-1-(4'-methoxyphenyl)-1,2-propanediol 
• 123-11-5 4-methoxy-benzaldehyde 
• 131029-02-2 (S)-1-(4-methoxyphenyl)propan-2-yl acetate 

Downstream Products

• 863666-27-7 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide D-tartrate 
• 106133-20-4 tamsulosin hydrochloride 
• 858583-36-5 1,2-bis(2-ethoxyphenoxy)ethane 
• 918867-88-6 5-((R)-2-{bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide 
• 106133-20-4 (R)-tamsulosin 
• 125961-36-6 HSR-175 hydrochloride 
• 1031281-18-1 (-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide 
• 133261-17-3 (R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide 
• 1262059-02-8 (-)-5-((2R)-2-{[2-(2-isopropoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide 
• 1262059-07-3 2-methoxy-5-((2R)-2-cis-{[(3-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-amino}propyl)benzenesulfonamide 
• 1262059-04-0 2-methoxy-5-((2R)-2-cis-{[(3-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-amino}propyl)benzenesulfonamide 
• 1262059-08-4 C₂₁H₃₄N₂O₅S 
• 1262059-03-9 (-)-5-[(2R)-2-({2-[2-(benzyloxy)phenoxy]ethyl}amino)propyl]-2-methoxybenzenesulfonamide 
• 1210430-94-6 5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate 

Relevant academic research and scientific papers

NOVEL PROCESS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 2-METHOXY-5-[(2R)-2-(4-ALKYLPIPERAZIN-L-YL)PROPYL]-BENZENESULFONAMIDE

Where R is C1-C3 alkyl, alkenyl A novel process for synthesis of compound of Formula 1 comprising steroselective catalytic reduction of compound of Formula IV under hydrogen gas pressure to obtain an intermediate compound of Formula II, which on coupling in presence of coupling agent and base in presence of organic solvent to obtain compound of Formula X, Formula X on reacting with deprotecting agent in presence of organic solvent results in formation of compound of Formula XI, condensation of Formula XI with alkyl halide results in formation of compound of Formula I.

Synthesis and α1-adrenoceptor antagonist activity of tamsulosin analogues

Tamsulosin (-)-1 is the most utilized α1-adrenoceptor antagonist in the benign prostatic hyperplasia therapy owing to its uroselective antagonism and capability in relieving both obstructive and irritative lower urinary tract symptoms. Here we report the synthesis and pharmacological study of the homochiral (-)-1 analogues (-)-2-(-)-5, bearing definite modifications in the 2-substituted phenoxyethylamino group in order to evaluate their influence on the affinity profile for α1-adrenoceptor subtypes. The benzyl analogue (-)-3, displaying a preferential antagonist profile for α1A-than α1D-and α1B- adrenoceptors, and a 12-fold higher potency at α1A- adrenoceptors with respect to the α1B subtype, may have improved uroselectivity compared to (-)-1.

Improved process for the preparation of tamsulosin hydrochloride

Ellman's sulfinamide reagent is used in asymmetric synthesis of Tamsulosin hydrochloride. The enantiomeric ratio achieved is 87:13. The crystallization of the same with dibenzoyl tartarate afforded the product 2 with 99.5% ee.

AN IMPROVED PROCESS FOR THE PREPARATION OF TAMSULOSIN HYDROCHLORIDE

The invention relates an improved process for preparing the (R)-(-)5-[2-[[2-(2-ethoxyphenoxyethyl]amino]propyl]-2-methoxybenzenesulfonamide of Formula (I): and its pharmaceutically acceptable salts.

Assymetric formal synthesis of (-)-formoterol and (-)-tamsulosin

Biologically important (2R)-2-amino-3-phenylpropanes consisted in commercial drugs including (R,R)-formoterol, and (R)-tamsulosin were prepared from chiral (2R)-aziridine-2-carboxylate without any chromatographic separation. Key reactions include regio- and stereoselective ring opening reaction of aziridin-2-yl-phenylmethanol and subsequent cyclization toward enantiopure 4,5-disubastitued oxazolidin-2-ones as synthetic intermediates.

PROCESS FOR THE PREPARATION OF TAMSULOSIN

The invention includes an improved process for producing tamsulosin comprising reacting 5-(2-aminopropyl)-2-methoxybenzenesulfonamide with 2-(o-ethoxyphenoxy)ethyl bromide in an organic phosphite solvent to obtain tamsulosin. Optically pure (R)- 5-(2-aminopropyl)-2- methoxybenzenesulfonamide can be employed to produce optically pure (R)-tamsulosin product. The organic phosphite solvent utilized in the reaction can include tri-alkyl phosphites such as triethyl phosphite, trimethyl phosphite, and tributyl phosphite. Additionally, processes for producing tamsulosin having a low concentration of by-product contaminants, such as 5-((R)-2- {Bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide, and the use of such by-products to monitor the chemical purity of tamsulosin, are provided.

A new enzymatic approach to (R)-Tamsulosin hydrochloride

An enantioselective baker's yeast mediated approach to the pharmacologically active (R)-enantiomer of Tamsulosin hydrochloride is reported.

A METHOD OF PREPARATION OF (R)-(-)-5(2-AMINOPROPYL)-2-METHOXYBENZENESULFONAMIDE

A method of preparation of (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide of formula I and its use for production tamsulosin. A protective group is introduced to N-[(1R)-2-(4-methoxyphenyl)-1-methylethyl]-N- [(1 R)-1-phenylethyl)]amine and the resulting amide of formula IX is chlorosulfonated and the resulting sulfochloride is converted to a sulfonamide of formula X, from which the compound of formula I is obtained by hydrogenation.

SYNTHESIS OF OPTICALLY PURE (R)-5-(2-AMINOPROPYL)-2-METHOXYBENZENESULPHONAMIDE

The present invention relates to a new process for the preparation of optically pure (R)-5-(2-aminopropyl)-2-methoxybenzenesulphonamide, which is an intermediate in the synthesis of tamsulosin.

METHOD FOR PRODUCING OPTICALLY ACTIVE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for simply producing (R)-(-)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide hydrochloride salt and an intermediate for the same at a reduced cost. SOLUTION: This method for producing the optically active compound expressed by chemical formula (6) comprises subjecting a compound expressed by chemical formula (5) to optical resolution with an optical resolution agent which has an optically active saccharide derivative as an asymmetry identifying part.