Silodosin supplier | CasNO.160970-64-9

Name
Silodosin
EINECS
CAS No. 160970-64-9
Article Data1
CAS DataBase
Density 1.249 g/cm³
Solubility
Melting Point
Formula C₂₅H₃₂F₃N₃O₄
Boiling Point 601.4 °C at 760 mmHg
Molecular Weight 495.542
Flash Point 317.5 °C
Transport Information
Appearance colorless to pink solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 97.05000
LogP 4.22730

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

: Benzoic acid-3-[7-cyano-5(R)-(2-{2-[2-(2,2,2-trifluoro-ethoxy)-phenoxy]-ethylamino}-propyl)-2,3-dihydro-indol-1-yl]-propyl ester

: 160970-64-9
1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; water / methanol / 2 h / 20 °C 2: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C View Scheme

: 1338365-54-0
5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole

: 160970-64-9
1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 20 °C 2: sodium hydroxide; water / methanol / 2 h / 20 °C 3: sodium hydroxide; water; dihydrogen peroxide / dimethyl sulfoxide / 0 - 25 °C View Scheme

: 160970-64-9
1-(3-hydroxypropyl)-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)indoline-7-carboxamide

: 160970-54-7
silodosin

Conditions

Conditions	Yield
In ethyl acetate at 15 - 55℃;	7.2g

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 .

Product Name

Silodosin

Synthetic route

Silodosin Chemical Properties

Silodosin History

Silodosin Specification

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