Pradaxa supplier | CasNO.872728-81-9

Name
Dabigatran Etexilate Mesylate
EINECS 828-727-6
CAS No. 872728-81-9
Article Data29
CAS DataBase
Density
Solubility
Melting Point
Formula C₃₄H₄₁N₇O₅·CH₄O₃S
Boiling Point 827.9 °C at 760 mmHg
Molecular Weight 723.85
Flash Point 454.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Dabigatran etexilate mesylate;N-[[2-[[[4-[[[(Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine ethyl ester monomethanesulfonat;
PSA 216.78000
LogP 6.96070

Synthetic route

: 211915-06-9
dabigatran etexilate

: 75-75-2
methanesulfonic acid

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
In acetone at 26 - 36℃; Industry scale;	98%
In acetone at 28 - 45℃; for 1h;	24 g

: 75-75-2
methanesulfonic acid

: 6092-54-2
n-hexyl chloroformate

: 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride salt

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Stage #1: n-hexyl chloroformate; 3-({2-[(4-carbamimidoyl-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-ylamino)propionic acid ethyl ester hydrochloride With triethylamine In chloroform Stage #2: methanesulfonic acid In acetone

...Expand

: 75-75-2
methanesulfonic acid

: 6092-54-2
n-hexyl chloroformate

: 3-({2-[(4-carbamimidoyl-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)-propionic acid ethyl ester dihydrochloride

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Stage #1: n-hexyl chloroformate; 3-({2-[(4-carbamimidoyl-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)-propionic acid ethyl ester dihydrochloride With triethylamine In chloroform at 20℃; Stage #2: methanesulfonic acid In acetone

...Expand

: 1-methyl-2-[N-(4-cyanophenyl)aminomethyl]benzimidazol-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide p-toluenesulfonate

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 18 h / -10 - 17 °C / Inert atmosphere 2: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 3: acetone / 1 h / 28 - 45 °C View Scheme

: 872728-85-3
1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 2: acetone / 1 h / 28 - 45 °C View Scheme

: 42288-26-6
(4-cyanophenyl)glycine

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Imidazole hydrochloride; 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 35 - 40 °C / Inert atmosphere 1.2: 1 h / Inert atmosphere; Reflux 1.3: 1 h / 85 - 90 °C / Inert atmosphere 2.1: hydrogenchloride / ethanol / 18 h / -10 - 17 °C / Inert atmosphere 3.1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 4.1: acetone / 1 h / 28 - 45 °C View Scheme
Multi-step reaction with 4 steps 1.1: Imidazole hydrochloride; 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 45 - 50 °C / Inert atmosphere 1.2: 1 h / 45 - 50 °C / Inert atmosphere 1.3: 6 h / Inert atmosphere; Reflux 2.1: hydrogenchloride / ethanol / 18 h / 0 - 17 °C 3.1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 4.1: acetone / 1 h / 28 - 45 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: Imidazole hydrochloride; 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 35 - 40 °C / Inert atmosphere
1.2: 1 h / Inert atmosphere; Reflux
1.3: 1 h / 85 - 90 °C / Inert atmosphere
2.1: hydrogenchloride / ethanol / 18 h / -10 - 17 °C / Inert atmosphere
3.1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C
4.1: acetone / 1 h / 28 - 45 °C
View Scheme

Multi-step reaction with 4 steps
1.1: Imidazole hydrochloride; 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 45 - 50 °C / Inert atmosphere
1.2: 1 h / 45 - 50 °C / Inert atmosphere
1.3: 6 h / Inert atmosphere; Reflux
2.1: hydrogenchloride / ethanol / 18 h / 0 - 17 °C
3.1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C
4.1: acetone / 1 h / 28 - 45 °C
View Scheme

: 212322-56-0
ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Imidazole hydrochloride; 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 35 - 40 °C / Inert atmosphere 1.2: 1 h / Inert atmosphere; Reflux 1.3: 1 h / 85 - 90 °C / Inert atmosphere 2.1: hydrogenchloride / ethanol / 18 h / -10 - 17 °C / Inert atmosphere 3.1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 4.1: acetone / 1 h / 28 - 45 °C View Scheme
Multi-step reaction with 4 steps 1.1: Imidazole hydrochloride; 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 45 - 50 °C / Inert atmosphere 1.2: 1 h / 45 - 50 °C / Inert atmosphere 1.3: 6 h / Inert atmosphere; Reflux 2.1: hydrogenchloride / ethanol / 18 h / 0 - 17 °C 3.1: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 4.1: acetone / 1 h / 28 - 45 °C View Scheme

Yield

: 211915-84-3
3-[[[2-[[(4-cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propionic acid ethyl ester

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 18 h / 0 - 17 °C 2: potassium carbonate / acetone; water / 1.5 h / 12 - 25 °C 3: acetone / 1 h / 28 - 45 °C View Scheme

: 75-75-2
methanesulfonic acid

: 6092-54-2
n-hexyl chloroformate

: C25H25N7O3*C7H8O3S

: 872728-81-9
dabigatran etexilate mesylate

Conditions

Conditions	Yield
Stage #1: n-hexyl chloroformate; C25H25N7O3*C7H8O3S With potassium carbonate In water; acetone at 5℃; for 1h; Stage #2: methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h;	35.1 g

...Expand

: 75-75-2
methanesulfonic acid

: 872728-81-9
dabigatran etexilate mesylate

: dabigatran etexilate bismesylate

Conditions

Conditions	Yield
In ethyl acetate at 20℃; Product distribution / selectivity;	99.9%

Pradaxa Specification

The Pradaxa, with the CAS registry number 872728-81-9, is also known as Dabigatran etexilate mesylate. It belongs to the product categories of Aromatics; Bases & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals. This chemical's molecular formula is C₃₄H₄₁N₇O₅·CH₄O₃S and molecular weight is 723.84. What's more, its systematic name is called Ethyl N-[(2-{[(4-{N'-[(hexyloxy)carbonyl]carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-2-pyridinyl-β-alaninate methanesulfonate (1:1).

Physical properties about Pradaxa are: (1)ACD/LogP: 5.133; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 4.81; (4)ACD/LogD (pH 7.4): 5.13; (5)ACD/BCF (pH 5.5): 2207.97; (6)ACD/BCF (pH 7.4): 4624.89; (7)ACD/KOC (pH 5.5): 6955.39; (8)ACD/KOC (pH 7.4): 14569.05; (9)#H bond acceptors: 12; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 18; (12)Polar Surface Area: 122.46 Å²; (13)Flash Point: 454.5 °C; (14)Enthalpy of Vaporization: 120.31 kJ/mol; (15)Boiling Point: 827.9 °C at 760 mmHg; (16)Vapour Pressure: 1.49E-27 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=S(=O)(O)C.O=C(OCC)CCN(c1ncccc1)C(=O)c4ccc2c(nc(n2C)CNc3ccc(C(=N\C(=O)OCCCCCC)\N)cc3)c4
(2) InChI: InChI=1S/C34H41N7O5.CH4O3S/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29;1-5(2,3)4/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44);1H3,(H,2,3,4)
(3) InChIKey: XETBXHPXHHOLOE-UHFFFAOYSA-N

Product Name

Dabigatran Etexilate Mesylate

Synthetic route

Pradaxa Specification

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