869477-96-3 Usage
Description
BI 1744 hydrochloride is a long-acting β2-adrenergic receptor agonist with high selectivity over the β1and β3-receptors. It is used for the long-term, once-daily maintenance treatment of chronic obstructive pulmonary disease (COPD). Administered by inhalation, it delivers significant bronchodilator effects within minutes and provides sustained improvement in lung function.
Uses
Used in Pharmaceutical Industry:
BI 1744 hydrochloride is used as a long-acting β2-adrenergic receptor agonist for treating patients with chronic obstructive pulmonary disease (COPD). It helps to relax smooth muscle cells in the airway, leading to improved lung function and reduced symptoms of COPD.
Synthesis
Commercial 20,50-dihydroxyacetophenone (122) was treated
with one equivalent of benzyl bromide and potassium carbonate
in methylisobutylketone (MIBK) to give the 50-monobenzylated
product in 76% yield. Subsequent nitration occurred at the 40-position
to provide nitrophenol 123 in 87% yield. Reduction of the nitro
group followed by subjection to chloroacetyl chloride resulted in
the construction of benzoxazine 124 in 82% yield. Next, monobromination
through the use of tetrabutylammonium tribromide
occurred at the acetophenone carbon to provide bromoketone
125, and this was followed by asymmetric reduction of the ketone
employing ()-DIP chloride to afford an intermediate bromohydrin,
which underwent conversion to the corresponding
epoxide 126 in situ upon treatment with aqueous NaOH. This
epoxide was efficiently formed in 85% yield and 98.3% enantiomeric
excess. Epoxide 126 underwent ring-opening upon subjection
to amine 127 to provide amino-alcohol 128 in in 84–90%
yield and 89.5–99.5% enantiomeric purity following salt formation
with HCl. Tertiary amine 127 was itself prepared in three steps by
reaction of ketone 129 with methylmagnesium chloride, Ritter
reaction of the tertiary alcohol with acetonitrile, and hydrolysis
of the resultant acetamide with ethanolic potassium hydroxide.
Hydrogenative removal of the benzyl ether within 128 followed
by recrystallization with methanolic isopropanol furnished olodaterol
hydrochloride (XVI) in 63–70% yield. Overall, the synthesis
of olodaterol hydrochloride required 10 total steps (7 linear) from
commercially available acetophenone 122.
Check Digit Verification of cas no
The CAS Registry Mumber 869477-96-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,9,4,7 and 7 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 869477-96:
(8*8)+(7*6)+(6*9)+(5*4)+(4*7)+(3*7)+(2*9)+(1*6)=253
253 % 10 = 3
So 869477-96-3 is a valid CAS Registry Number.
869477-96-3Relevant articles and documents
Preparation method of olodaterol and salts thereof
-
, (2021/04/03)
The invention relates to a preparation method of olodaterol and salts thereof, which comprises the following steps: in a solvent, carrying out oxidation and nucleophilic addition reaction on a compound shown in a formula I to obtain a compound shown in a
Crystal form C of olodaterol hydrochloride and preparation method thereof
-
Paragraph 0063; 0068; 0069, (2018/11/27)
The invention relates to a crystal form C of a long-acting beta2 adrenergic agonist olodaterol hydrochloride and a preparation method thereof and a pharmaceutical composition containing the crystal form C. The crystal form is represented by the characteri
A Process for Preparing Olodaterol and Intermediates Thereof
-
, (2017/09/24)
The present invention relates to a process for preparing olodaterol and intermediates thereof. The process comprises of forming compound of Formula 1 by reacting compound of Formula 2 or its acid salt with compound of Formula 3 in the presence of an organ