Indacaterol interMediate

Base Information

• Chemical Name: Indacaterol interMediate
• CAS No.: 435273-75-9
• Molecular Formula: C31H34N2O3
• Molecular Weight: 482.623
• Mol file: 435273-75-9.mol

Synonyms:(R)-5-[2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl;

Chemical Property of Indacaterol interMediate

Chemical Property:

• Boiling Point: 734.1±60.0 °C(Predicted)
• PKA: 10.86±0.70(Predicted)
• PSA: 74.35000
• Density: 1.23
• LogP: 5.41320
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

5-[(1R)-2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(phenylmethoxy)-2(1H)-quinolinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-[(1R)-2-[(5,6-Diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(phenylmethoxy)-2(1H)-quinolinone is used as a reactant in the preparation of Indacaterol (I499745), a β-adrenoreceptor agonist.

Technology Process of Indacaterol interMediate

There total 19 articles about Indacaterol interMediate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one (530084-79-8) + 5,6-diethyl-2,3-dihydro-1H-inden-2-amine (312753-70-1) → (R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one (435273-75-9)

Guidance literature:

With triethylamine; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

Reference yield: 79.3%

5-(R)-(2-amino-1-hydroxy-ethyl)-8-phenylmethoxy-(1H)-quinolin-2-one (774222-23-0) + 2-chloro-5,6-diethylindan → (R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one (435273-75-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; sodium iodide; In N,N-dimethyl-formamide; at 20 - 90 ℃;

Reference yield: 68.7%

5,6-diethyl-2,3-dihydro-1H-inden-2-amine (312753-70-1) + benzoic acid (65-85-0,8013-63-6) → (R)-8-(benzyloxy)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-indole-2-yl)amino]-1-hydroxyethyl]quinolin-2(1H)-one (435273-75-9) + 8-(benzyloxy)-5-(1-(5,6-diethyl-2,3-dihydro-1H-inden-2-ylamino)-2-hydroxyethyl)quinolin-2(1H)-one + 8-(phenylmethoxy)-5-[(R)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-(1H)-quinolin-2-one benzoate + C49H49N3O6

Guidance literature:

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone; 5,6-diethyl-2,3-dihydro-1H-inden-2-amine; In diethylene glycol dimethyl ether; at 110 ℃; for 15h;

benzoic acid; In ethanol; diethylene glycol dimethyl ether; at 0 - 70 ℃;

upstream raw materials:

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

benzoic acid

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

5-(2,2-Dihydroxyacetyl)-8-(benzyloxy)-carbostyril

Downstream raw materials:

indacaterol

indacaterol maleate

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

indacaterol maleate

Refernces

• 1、 -. "A maleic acid yin dutrow intermediate and its preparation and use". Paragraph 0061-0062. . Retrieved 2019/05/16.
• 2、 -. "A Process for Preparing Indacaterol and Salts Thereof". . . Retrieved 2018/08/20.