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872728-81-9

Basic Information
CAS No.: 872728-81-9
Name: Pradaxa
Molecular Structure:
Molecular Structure of 872728-81-9 (Pradaxa)
Formula: C34H41N7O5·CH4O3S
Molecular Weight: 723.84
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;
EINECS: 828-727-6
Density:
Melting Point:
Boiling Point: 827.9 °C at 760 mmHg
Flash Point: 454.5 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
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
ConditionsYield
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
ConditionsYield
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
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
ConditionsYield
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

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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
ConditionsYield
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
ConditionsYield
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
75-75-2

methanesulfonic acid

872728-81-9

dabigatran etexilate mesylate

dabigatran etexilate bismesylate

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

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