Product Name

  • Name

    TMC-207

  • EINECS 1308068-626-2
  • CAS No. 843663-66-1
  • Article Data13
  • CAS DataBase
  • Density 1.322 g/cm3
  • Solubility
  • Melting Point 104 °C
  • Formula C32H31BrN2O2
  • Boiling Point 702.7 °C at 760 mmHg
  • Molecular Weight 555.514
  • Flash Point 378.8 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 843663-66-1 (TMC-207)
  • Hazard Symbols
  • Synonyms TMC-207;1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol;1-(1R)-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-(2S)-(naphthalen-1-yl)-1-phenyl-butan-2-ol;3-Quinolineethanol, 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-;
  • PSA 45.59000
  • LogP 7.13050

Synthetic route

(3S,4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl-4-methylbenzenesulfonate
1229443-16-6

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

dimethyl amine
124-40-3

dimethyl amine

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 40℃; for 10h; Inert atmosphere;62%
rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

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

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

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Stage #1: 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;
Stage #2: In acetone at 20 - 30℃; for 2.75 - 4h; Heating / reflux;
Stage #3: With potassium carbonate In water; toluene at 80 - 85℃; for 0.0833333 - 0.25h; Purification / work up;		39%
1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20℃; for 3h; Reflux;39%
Stage #1: 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20℃; for 2h; Resolution of racemate; Reflux;
Stage #2: With potassium carbonate In toluene Resolution of racemate; Reflux;		39%
3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

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

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

C

(R,S)-bedaquiline

(R,S)-bedaquiline

Conditions
ConditionsYield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -20℃; for 0.25h; Nitrogen atmosphere;
Stage #2: 3-benzyl-6-bromo-2-methoxyquinoline In tetrahydrofuran at -70℃; for 0.5h;
Stage #3: 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone With water more than 3 stages;
...Expand
(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone
1298044-25-3

(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
1.2: 0.5 h
2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
3.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol
1298044-27-5

(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
2: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
3: triethylamine / dichloromethane / 3 h / 0 - 20 °C
4: tetrahydrofuran / 24 h / 45 °C
View Scheme
C30H24BrNO3
1298044-29-7

C30H24BrNO3

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: tetrahydrofuran / 24 h / 45 °C
View Scheme
(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol
1298044-31-1

(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: tetrahydrofuran / 24 h / 45 °C
View Scheme
(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl methanesulfonate
1298044-33-3

(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl methanesulfonate

dimethyl amine
124-40-3

dimethyl amine

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
In tetrahydrofuran at 45℃; for 24h;
...Expand
ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate
1298044-13-9

ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 - 20 °C
1.2: 4 h
2.1: methanol / 8 h / 80 °C
3.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
3.2: 4 h / -20 °C
4.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
4.2: 3 h / -40 °C
4.3: 3 h
5.1: / dichloromethane / 1 h / 0 - 20 °C
6.1: diethyl ether / 1 h / 0 °C
7.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
8.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
8.2: 0.5 h
9.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
10.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
11.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
12.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(E)-3-(6-bromo-2-chloroquinolin-3-yl)prop-2-en-1-ol
1298044-15-1

(E)-3-(6-bromo-2-chloroquinolin-3-yl)prop-2-en-1-ol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: methanol / 8 h / 80 °C
2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
2.2: 4 h / -20 °C
3.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
3.2: 3 h / -40 °C
3.3: 3 h
4.1: / dichloromethane / 1 h / 0 - 20 °C
5.1: diethyl ether / 1 h / 0 °C
6.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
7.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
7.2: 0.5 h
8.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
9.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
10.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
11.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(E)-3-(6-bromo-2-methoxyquinolin-3-yl)prop-2-en-1-ol
1298044-17-3

(E)-3-(6-bromo-2-methoxyquinolin-3-yl)prop-2-en-1-ol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
1.2: 4 h / -20 °C
2.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
2.2: 3 h / -40 °C
2.3: 3 h
3.1: / dichloromethane / 1 h / 0 - 20 °C
4.1: diethyl ether / 1 h / 0 °C
5.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
6.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
6.2: 0.5 h
7.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
8.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
9.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
10.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
[(2S,3S)-3-(6-bromo-2-methoxyquinolin-3-yl)oxiran-2-yl]methanol
1298044-10-6

[(2S,3S)-3-(6-bromo-2-methoxyquinolin-3-yl)oxiran-2-yl]methanol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
1.2: 3 h / -40 °C
1.3: 3 h
2.1: / dichloromethane / 1 h / 0 - 20 °C
3.1: diethyl ether / 1 h / 0 °C
4.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
5.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
5.2: 0.5 h
6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
7.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
8.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
9.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(2R,3R)-3-(6-bromo-2-methoxyquinolin-3-yl)-3-phenylpropane-1,2-diol
1298044-19-5

(2R,3R)-3-(6-bromo-2-methoxyquinolin-3-yl)-3-phenylpropane-1,2-diol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: / dichloromethane / 1 h / 0 - 20 °C
2.1: diethyl ether / 1 h / 0 °C
3.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
4.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
4.2: 0.5 h
5.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
6.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
8.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
C18H14BrNO2
1298044-21-9

C18H14BrNO2

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: diethyl ether / 1 h / 0 °C
2.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
3.2: 0.5 h
4.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
5.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
6.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
7.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanol
1298044-24-2

(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanol

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
2.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
2.2: 0.5 h
3.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
4.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
5.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
6.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
6-bromo-2-chloro-3-formylquinoline
73568-35-1

6-bromo-2-chloro-3-formylquinoline

A

bedaquiline
843663-66-1

bedaquiline

B

(1R,2R)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
857086-94-3

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

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C
1.2: 2 h
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 - 20 °C
2.2: 4 h
3.1: methanol / 8 h / 80 °C
4.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.67 h / -20 °C / Molecular sieve
4.2: 4 h / -20 °C
5.1: copper(l) cyanide / tetrahydrofuran; diethyl ether / 1 h / -40 °C
5.2: 3 h / -40 °C
5.3: 3 h
6.1: / dichloromethane / 1 h / 0 - 20 °C
7.1: diethyl ether / 1 h / 0 °C
8.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
9.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / 20 °C
9.2: 0.5 h
10.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 2 h / 20 °C
11.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
12.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
13.1: tetrahydrofuran / 24 h / 45 °C
View Scheme
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

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

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: 12 h / -78 - -40 °C
2.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
2.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
...Expand
1'-naphthacetophenone
941-98-0

1'-naphthacetophenone

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / ethanol / 12 h / Reflux; Inert atmosphere
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 12 h / -78 - -40 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
3.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol

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

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Stage #1: rac-(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol With (R)-1,1'-binaphthyl-2,2'-phosphoric acid In dimethyl sulfoxide; acetone at 20℃; for 2h; Reflux; Inert atmosphere;
Stage #2: With potassium carbonate In water; toluene at 80℃; for 0.5h; Inert atmosphere;		A 0.35 g
B n/a
4-bromo-aniline
106-40-1

4-bromo-aniline

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine / 0 - 20 °C / Inert atmosphere
2.1: trichlorophosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
3.1: methanol / Reflux; Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: 12 h / -78 - -40 °C
5.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
5.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
N-(4-bromophenyl)-3-phenylpropanamide
316146-27-7

N-(4-bromophenyl)-3-phenylpropanamide

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trichlorophosphate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
2.1: methanol / Reflux; Inert atmosphere
3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
3.2: 12 h / -78 - -40 °C
4.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
4.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
3-benzyl-6-bromo-2-chloro-quinoline
654655-68-2

3-benzyl-6-bromo-2-chloro-quinoline

A

bedaquiline
843663-66-1

bedaquiline

B

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
654655-80-8

1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol / Reflux; Inert atmosphere
2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 12 h / -78 - -40 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Reflux; Inert atmosphere
3.2: 0.5 h / 80 °C / Inert atmosphere
View Scheme
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

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

A

bedaquiline
843663-66-1

bedaquiline

B

(R,S)-bedaquiline

(R,S)-bedaquiline

C

C32H31BrN2O2

C32H31BrN2O2

Conditions
ConditionsYield
With n-butyllithium; (S)-N-benzylprolinol; lithium diisopropyl amide In tetrahydrofuran; hexane; n-heptane; ethylbenzene at -78 - -72℃; for 3h; Reagent/catalyst; Inert atmosphere;A n/a
B n/a
C n/a
...Expand
3-dimethylamino-1-(naphthalene-1-yl)-prop-2-en-1-one

3-dimethylamino-1-(naphthalene-1-yl)-prop-2-en-1-one

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
1.2: 12 h
2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h / 20 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 3 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
1.2: 12 h
2.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 12 h / 20 °C
3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Resolution of racemate; Reflux
3.2: Resolution of racemate; Reflux
View Scheme
1'-naphthacetophenone
941-98-0

1'-naphthacetophenone

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 24 h / 120 °C
2.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
2.2: 12 h
3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h / 20 °C
4.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 3 h / 20 °C / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 24 h / 100 °C
2.1: lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -20 °C
2.2: 12 h
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 12 h / 20 °C
4.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid / acetone; dimethyl sulfoxide / 2 h / 20 °C / Resolution of racemate; Reflux
4.2: Resolution of racemate; Reflux
View Scheme
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one
2752-87-6

3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
With acetic acid; lithium diisopropyl amide In tetrahydrofuran at -80 - -70℃; Inert atmosphere;9.45 g
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone
10320-49-7

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

A

bedaquiline
843663-66-1

bedaquiline

B

(R,S)-bedaquiline

(R,S)-bedaquiline

Conditions
ConditionsYield
Stage #1: 3-benzyl-6-bromo-2-methoxyquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 3-(dimethylamino)-1-(1-naphthalenyl)-1-propanone In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #3: With acetic acid In tetrahydrofuran at 0℃; Overall yield = 84.4 percent;
...Expand
hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

bedaquiline
843663-66-1

bedaquiline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 5 - 10 °C
2.1: trichlorophosphate / acetonitrile / 3 h / 75 - 80 °C
3.1: 12 h / 60 - 65 °C
4.1: lithium diisopropyl amide / tetrahydrofuran / -75 - -70 °C
4.2: 2.5 h / -75 - -70 °C
View Scheme
bedaquiline
843663-66-1

bedaquiline

citric acid
77-92-9

citric acid

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

Conditions
ConditionsYield
In isopropyl alcohol at 50 - 80℃; for 1h;96.6%
bedaquiline
843663-66-1

bedaquiline

(1R,2S)-4-(dimethylamino)-1-(2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

(1R,2S)-4-(dimethylamino)-1-(2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; triethylamine In tetrahydrofuran at 30℃; under 760.051 Torr; for 4h; Solvent; Temperature;90%
bedaquiline
843663-66-1

bedaquiline

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate
845533-86-0

[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate

Conditions
ConditionsYield
In isopropyl alcohol at 20 - 70℃; for 18h; Heating / reflux;82%
In isopropyl alcohol at 70 - 80℃; for 1h;
In isopropyl alcohol at 75 - 80℃;15 g
In propan-1-ol; acetone
bedaquiline
843663-66-1

bedaquiline

m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

C39H37BrN2O3
1032266-07-1

C39H37BrN2O3

Conditions
ConditionsYield
Stage #1: bedaquiline With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 1h;
Stage #2: m-bromobenzoic aldehyde In tetrahydrofuran; hexane at -70℃; for 1h;
Stage #3: With water In tetrahydrofuran; hexanes at -40℃;		37%
bedaquiline
843663-66-1

bedaquiline

citric acid
77-92-9

citric acid

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol citrate

Conditions
ConditionsYield
In isopropyl alcohol37%
bedaquiline
843663-66-1

bedaquiline

tartaric acid
87-69-4

tartaric acid

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol tartrate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol tartrate

Conditions
ConditionsYield
In acetonitrile34%
bedaquiline
843663-66-1

bedaquiline

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol sulphate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol sulphate

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol33%
bedaquiline
843663-66-1

bedaquiline

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol phosphate

(1R,2S)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol phosphate

Conditions
ConditionsYield
With phosphoric acid In tetrahydrofuran33%

6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol Specification

The 6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol with the CAS number 843663-66-1 is also called TMC-207. Both the systematic name and IUPAC name are 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol. Its molecular formula is C32H31BrN2O2. This chemical is a diarylquinoline Antitubercular Agent.

The properties of the 6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol are: (1)ACD/LogP: 7.03; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 4.1; (4)ACD/LogD (pH 7.4): 5.5; (5)ACD/BCF (pH 5.5): 151.27; (6)ACD/BCF (pH 7.4): 3776.5; (7)ACD/KOC (pH 5.5): 185.09; (8)ACD/KOC (pH 7.4): 4620.73; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 34.59 Å2; (13)Index of Refraction: 1.666; (14)Molar Refractivity: 156.19 cm3; (15)Molar Volume: 420 cm3; (16)Polarizability: 61.92×10-24cm3; (17)Surface Tension: 52.6 dyne/cm; (18)Enthalpy of Vaporization: 107.98 kJ/mol; (19)Vapour Pressure: 1.01×10-20 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Brc1ccc2nc(OC)c(cc2c1)C(c3ccccc3)C(O)(c5c4ccccc4ccc5)CCN(C)C
(2)InChI: InChI=1/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3
(3)InChIKey: QUIJNHUBAXPXFS-UHFFFAOYAJ

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