Bedaquiline IMpurity

Base Information

• Chemical Name: Bedaquiline IMpurity
• CAS No.: 857086-92-1
• Molecular Formula: C₃₂H₃₁BrN₂O₂
• Molecular Weight: 555.514
• Mol file: 857086-92-1.mol

Synonyms:

Chemical Property of Bedaquiline IMpurity

Chemical Property:

• Boiling Point: 702.7±60.0 °C(Predicted)
• PKA: 13.05±0.29(Predicted)
• Density: 1.322±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bedaquiline IMpurity

There total 91 articles about Bedaquiline IMpurity 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: 62.0%

(3S,4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl-4-methylbenzenesulfonate (1229443-16-6) + dimethyl amine (124-40-3) → bedaquiline (843663-66-1,654653-93-7,857086-92-1)

Guidance literature:

In water; N,N-dimethyl-formamide; at 40 ℃; for 10h; Inert atmosphere;

DOI:10.1021/ja103183r

Reference yield: 39.0%

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol (654655-80-8,654653-93-7,857086-92-1) → bedaquiline (843663-66-1,654653-93-7,857086-92-1)

Guidance literature:

With (R)-1,1'-binaphthyl-2,2'-phosphoric acid; In dimethyl sulfoxide; acetone; at 20 ℃; for 3h; Reflux;

Reference yield: 39.0%

rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol (654653-93-7,857086-92-1) + 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol*(11bR)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide (916329-20-9) → bedaquiline (843663-66-1,654653-93-7,857086-92-1)

Guidance literature:

rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol; 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol*(11bR)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide; With (R)-1,1'-binaphthyl-2,2'-phosphoric acid; In dimethyl sulfoxide; acetone; at 20 - 50 ℃; for 3.16667 - 5.75h; Heating / reflux; Resolution of racemate;

In acetone; at 20 - 30 ℃; for 2.75 - 4h; Heating / reflux;

With potassium carbonate; In water; toluene; at 80 - 85 ℃; for 0.0833333 - 0.25h; Purification / work up;

upstream raw materials:

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone

rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol*(11bR)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide

(3S,4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl-4-methylbenzenesulfonate

Downstream raw materials:

C₃₉H₃₅BrN₂O₃

Refernces

• 1、 -. "Method for preparing bisarylquinoline antibiotics by optical resolution (by machine translation)". Paragraph 0084-0085. . Retrieved 2020/02/27.
• 2、 Bogandowich-Knipp, Susan,Byrn, Stephen R.,Clase, Kari L.,Okezue, Mercy,Purcell, Dale K.,Smith, Daniel,Smith, Pamela,Zeller, Matthias. "Crystal structures of salts of bedaquiline". . p. 1010 - 1023. Retrieved 2020/11/13.