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Indacaterol
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Name

Indacaterol

 EINECS 691-091-1
CAS No. 312753-06-3 Density 1.27 g/cm3
PSA 85.35000 LogP 3.53980
Solubility N/A Melting Point N/A
Formula C24H28N2O3 Boiling Point 660.3 °C at 760 mmHg
Molecular Weight 392.498 Flash Point 353.1 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 312753-06-3 (Indacaterol) Hazard Symbols N/A
Synonyms

QAB 149;5-[(1R)-2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxyquinolin-2(1H)-one;

 

Indacaterol Synthetic route

indacaterol maleate

312753-06-3

indacaterol

Conditions
ConditionsYield
With lithium hydroxide monohydrate In methanol at 35℃; for 1h; Reagent/catalyst;99.84%
435273-75-9

(R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one

312753-06-3

indacaterol

Conditions
ConditionsYield
Stage #1: (R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 2h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In ethanol at 40℃; under 757.576 Torr; for 4h;		97%
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 20℃;85%
With palladium 10% on activated carbon; hydrogen In methanol at 19 - 22℃; for 1h; Inert atmosphere;83%

5-[(1R)-2-[N-benzyl-(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(benzyloxy)-2(1H)-quinolone

312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid In methanol at 20℃;86.2%
With palladium 10% on activated carbon; hydrogen; acetic acid at 40℃; under 15201 Torr; Pressure; Reagent/catalyst; Temperature;

(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one hydrochloride

312753-06-3

indacaterol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 25 - 30℃; under 2250.23 - 3000.3 Torr; for 4h;85.5%

5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-triethylsilyloxyethyl]-8-(benzyloxy)-2(1H)-quinolone

312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid; tetra-n-butylammoniumfluoride trihydrate In methanol at 20℃;84.5%

5-[(1R)-2-[N-benzyl-(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-triethylsilyloxyethyl]-8-(benzyloxy)-2(1H)-quinolone

312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; acetic acid; tetra-n-butylammoniumfluoride trihydrate In methanol at 20℃;83.7%
753498-33-8

8-(phenylmethoxy)-5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-(1H)-quinolin-2-one tartrate

312753-06-3

indacaterol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol under 225.023 Torr; Inert atmosphere;77%
With 5%-palladium/activated carbon; hydrogen In methanol under 225.023 Torr; Inert atmosphere;77%

5-{2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl}-8-hydroxy-1H-quinolin-2-one

312753-06-3

indacaterol

Conditions
ConditionsYield
With triethylamine In ethanol; hexane at 25℃; Resolution of racemate;49%

(R)-5- [2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-benzyloxy-1H-quinolin-2-one benzoic acid salt

312753-06-3

indacaterol

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In acetic acid for 2 - 8h;
With hydrogen; 5%-palladium/activated carbon In acetic acid for 2 - 8h;
312753-70-1

5,6-diethyl-2,3-dihydro-1H-inden-2-amine

312753-06-3

indacaterol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid; -butyl vinyl ether / tetrahydrofuran; toluene / 0.5 h / 20 - 25 °C / Molecular sieve
1.2: 100 °C
2.1: 5%-palladium/activated carbon; hydrogen / methanol / 225.02 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: Chiralcel AS-V / aq. phosphate buffer; acetonitrile / 25 °C / Resolution of racemate
3.1: 5%-palladium/activated carbon; hydrogen / ethanol / 2 h / 20 °C
3.2: 4 h / 40 °C / 757.58 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 1 h / 20 °C
1.2: 16 h / 0 - 20 °C
2.1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 - 40 °C / 757.58 Torr
3.1: triethylamine / ethanol; hexane / 25 °C / Resolution of racemate
View Scheme
Multi-step reaction with 4 steps
1: sodium cyanoborohydride / ethanol / 4 h / -25 - 80 °C / Inert atmosphere
2: sodium carbonate; potassium iodide / acetonitrile / 24 h / -25 - 80 °C
3: (-)-diisopinocamphenylborane chloride / dichloromethane; tetrahydrofuran / 25 h / 10 - 20 °C
4: hydrogen; acetic acid; palladium 10% on activated carbon / 40 °C / 15201 Torr
View Scheme
Multi-step reaction with 4 steps
1: butan-1-ol / 3 h / 100 - 110 °C
2: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 0 - 3 °C / Inert atmosphere
3: potassium carbonate / water; methanol / 1 h
4: acetic acid; palladium 10% on activated carbon; hydrogen / methanol / 6 h / 0 - 8 °C / 750.08 - 1500.15 Torr / Inert atmosphere
View Scheme

Indacaterol Specification

The 2(1H)-Quinolinone,5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-, with the CAS registry number 312753-06-3, is also known as 5-(2-(5,6-Diethylindan-2-ylamino)-1-hydroxyethyl)-8-hydroxy-1H-quinolin-2-one. This chemical's molecular formula is C24H28N2O3 and molecular weight is 392.49072. Its IUPAC name is called 5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one. This chemical's classification code is Treatment of COPD.

Physical properties of 2(1H)-Quinolinone,5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-: (1)ACD/LogP: 3.88; (2)ACD/LogD (pH 5.5): 0.99; (3)ACD/LogD (pH 7.4): 2.45; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 19.5; (6)ACD/KOC (pH 5.5): 3.96; (7)ACD/KOC (pH 7.4): 114.74; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 8; (11)Index of Refraction: 1.659; (12)Molar Refractivity: 113.26 cm3; (13)Molar Volume: 306.8 cm3; (14)Surface Tension: 63.9 dyne/cm; (15)Density: 1.27 g/cm3; (16)Flash Point: 353.1 °C; (17)Enthalpy of Vaporization: 102.09 kJ/mol; (18)Boiling Point: 660.3 °C at 760 mmHg; (19)Vapour Pressure: 2.47E-18 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCC1=C(C=C2CC(CC2=C1)NCC(C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC
(2)Isomeric SMILES: CCC1=C(C=C2CC(CC2=C1)NC[C@@H](C3=C4C=CC(=O)NC4=C(C=C3)O)O)CC
(3)InChI: InChI=1S/C24H28N2O3/c1-3-14-9-16-11-18(12-17(16)10-15(14)4-2)25-13-22(28)19-5-7-21(27)24-20(19)6-8-23(29)26-24/h5-10,18,22,25,27-28H,3-4,11-13H2,1-2H3,(H,26,29)/t22-/m0/s1
(4)InChIKey: QZZUEBNBZAPZLX-QFIPXVFZSA-N

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