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Silodosin
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Name

Silodosin

 EINECS N/A
CAS No. 160970-64-9 Density 1.249 g/cm3
PSA 97.05000 LogP 4.22730
Solubility N/A Melting Point N/A
Formula C25H32F3N3O4 Boiling Point 601.4 °C at 760 mmHg
Molecular Weight 495.542 Flash Point 317.5 °C
Transport Information N/A Appearance colorless to pink solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 160970-64-9 (Silodosin) Hazard Symbols N/A
Synonyms

1H-Indole-7-carboxamide,2,3-dihydro-1-(3-hydroxypropyl)-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-;2,3-Dihydro-1-(3-hydroxypropyl)-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carboxamide;

Article Data 1

Silodosin Synthetic route

1-(3-hydroxypropyl)-5(R)-[2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]-ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
With water; dihydrogen peroxide; sodium hydroxide In dimethyl sulfoxide at 0 - 25℃;87%

C22H25N3O5

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
2: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
4: sodium hydroxide; water / methanol / 2 h / 20 °C
5: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme

3-(indolin-1-yl)propan-1-ol

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: triethylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere
2.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 80 °C / Inert atmosphere
3.1: ammonium acetate; acetic acid / 4 h / 80 °C
4.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
5.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
5.2: 2 h / 0 - 80 °C / Inert atmosphere
6.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
7.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
8.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
9.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
10.1: sodium hydroxide; water / methanol / 2 h / 20 °C
11.1: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme

3-(indolin-1-yl)propyl benzoate

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere
1.2: 2 h / 0 - 80 °C / Inert atmosphere
2.1: ammonium acetate; acetic acid / 4 h / 80 °C
3.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
4.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
4.2: 2 h / 0 - 80 °C / Inert atmosphere
5.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
6.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
7.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
8.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
9.1: sodium hydroxide; water / methanol / 2 h / 20 °C
10.1: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme
350797-52-3

1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: ammonium acetate; acetic acid / 4 h / 80 °C
2.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
3.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 80 °C / Inert atmosphere
4.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
5.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
6.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
7.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
8.1: sodium hydroxide; water / methanol / 2 h / 20 °C
9.1: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme
350797-53-4

1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
2.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 80 °C / Inert atmosphere
3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
4.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
6.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
7.1: sodium hydroxide; water / methanol / 2 h / 20 °C
8.1: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme
496-15-1

1-indoline

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: potassium carbonate / acetonitrile / 12 h / 90 °C
2.1: triethylamine / dichloromethane / 8 h / 0 - 25 °C / Inert atmosphere
3.1: trichlorophosphate / 1,2-dichloro-ethane / 1 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 80 °C / Inert atmosphere
4.1: ammonium acetate; acetic acid / 4 h / 80 °C
5.1: sodium tetrahydroborate / dichloromethane; methanol / 1 h / 0 - 25 °C
6.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
6.2: 2 h / 0 - 80 °C / Inert atmosphere
7.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
8.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
9.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
10.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
11.1: sodium hydroxide; water / methanol / 2 h / 20 °C
12.1: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme
350797-54-5

1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: trichlorophosphate / 1 h / 0 °C / Inert atmosphere
1.2: 2 h / 0 - 80 °C / Inert atmosphere
2.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
3.1: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
4.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
5.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
6.1: sodium hydroxide; water / methanol / 2 h / 20 °C
7.1: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme
350797-55-6

1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 12 h / 70 °C
2: acetic anhydride / tetrahydrofuran / 24 h / 70 °C
3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
4: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
5: sodium hydroxide; water / methanol / 2 h / 20 °C
6: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme
350797-56-7

1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole

160970-64-9

1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 48 h / 40 °C
2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C
3: sodium hydroxide; water / methanol / 2 h / 20 °C
4: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C
View Scheme

Silodosin Chemical Properties

Molecule structure of Silodosin (CAS NO.160970-64-9):

IUPAC Name: 1-(3-Hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-2,3-dihydroindole-7-carboxamide 
Molecular Weight: 495.53449 g/mol
Molecular Formula: C25H32F3N3O4 
Density: 1.249 g/cm3 
Boiling Point: 601.4 °C at 760 mmHg 
Flash Point: 317.5 °C
Index of Refraction: 1.552
Molar Refractivity: 126.82 cm3
Molar Volume: 396.6 cm3
Surface Tension: 45.5 dyne/cm 
Enthalpy of Vaporization: 94.11 kJ/mol
Vapour Pressure: 2.58E-15 mmHg at 25 °C
XLogP3-AA: 3.6
H-Bond Donor: 3
H-Bond Acceptor: 9
Rotatable Bond Count: 13
Tautomer Count: 2
Exact Mass: 495.234491
MonoIsotopic Mass: 495.234491
Topological Polar Surface Area: 97
Heavy Atom Count: 35
Canonical SMILES: CC(CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
Isomeric SMILES: C[C@H](CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
InChI: InChI=1S/C25H32F3N3O4/c1-17(30-8-12-34-21-5-2-3-6-22(21)35-16-25(26,27)28)13-18-14-19-7-10-31(9-4-11-32)23(19)20(15-18)24(29)33/h2-3,5-6,14-15,17,30,32H,4,7-13,16H2,1H3,(H2,29,33)/t17-/m1/s1
InChIKey: PNCPYILNMDWPEY-QGZVFWFLSA-N

Silodosin History

In May 2006, Silodosin (CAS NO.160970-64-9) received its first marketing approval under the tradename Urief, which is jointly marketed by Daiichi Sankyo Pharmaceutical Co., Ltd and Kissei Pharmaceutical Co., Ltd.. In 2004, Kissei licensed the US, Canadian, and Mexican rights for silodosin to Watson Pharmaceuticals, Inc.. On February 12, 2008, Watson announced that the New Drug Application submitted to the United States Food and Drug Administration for silodosin has been accepted for filing. FDA approved this drug on October 9th, 2008. Silodosin is marketed under the tradename Rapaflo.

Silodosin Specification

 Silodosin (CAS NO.160970-64-9) is also named as Rapaflo ; Rapflo ; UNII-CUZ39LUY82 ; (-)-1-(3-Hydroxypropyl)-5-((2R)-2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)-2,3-dihydro-1H-indole-7-carboxamide ; 160970-54-7 .

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