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Name	6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol	EINECS	1308068-626-2
CAS No.	843663-66-1	Density	1.322 g/cm³
PSA	45.59000	LogP	7.13050
Solubility	N/A	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	N/A	Appearance	N/A
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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-;	Article Data	13

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

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

: 124-40-3
dimethyl amine

: 843663-66-1
bedaquiline

Conditions

Conditions	Yield
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

: 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

: 843663-66-1
bedaquiline

Conditions

Conditions	Yield
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%

Yield

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%

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

: 843663-66-1
bedaquiline

Conditions

Conditions	Yield
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%

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

A: 843663-66-1
bedaquiline

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

C: (R,S)-bedaquiline

Conditions

Conditions	Yield
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;

: 1298044-25-3
(2R)-2-(6-bromo-2-methoxyquinolin-3-yl)-1-(naphthalen-1-yl)-2-phenylethanone

A: 843663-66-1
bedaquiline

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

Conditions

Conditions	Yield
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

: 1298044-27-5
(1R)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(naphthalen-1-yl)-1-phenylpent-4-en-2-ol

A: 843663-66-1
bedaquiline

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

Conditions

Conditions	Yield
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

: 1298044-29-7
C30H24BrNO3

A: 843663-66-1
bedaquiline

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

Conditions

Conditions	Yield
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

: 1298044-31-1
(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-(naphthalen-1-yl)-4-phenylbutane-1,3-diol

A: 843663-66-1
bedaquiline

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2: tetrahydrofuran / 24 h / 45 °C View Scheme

: 1298044-33-3
(4R)-4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl methanesulfonate

: 124-40-3
dimethyl amine

A: 843663-66-1
bedaquiline

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

Conditions

Conditions	Yield
In tetrahydrofuran at 45℃; for 24h;

: 1298044-13-9
ethyl (E)-3-(6-bromo-2-chloroquinolin-3-yl)acrylate

A: 843663-66-1
bedaquiline

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

Conditions

Conditions	Yield
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

Yield

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

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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