Dabigatran etexilate supplier | CasNO.211915-06-9

Name
Dabigatran etexilate
EINECS 606-722-8
CAS No. 211915-06-9
Article Data53
CAS DataBase
Density 1.24 g/cm³
Solubility
Melting Point 128-129°
Formula C₃₄H₄₁N₇O₅
Boiling Point 827.9 °C at 760 mmHg
Molecular Weight 627.743
Flash Point 454.5 °C
Transport Information
Appearance white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Ethyl 3-(((2-(((4-((((hexyloxy)carbonyl)amino)iminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)(pyridin-2-yl)amino)propanoate;
PSA 154.03000
LogP 6.37590

Synthetic route

: 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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Stage #1: 3-({2-[(4-carbamimidoyl-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)-propionic acid ethyl ester dihydrochloride With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.333333h; Stage #2: n-hexyl chloroformate In tetrahydrofuran; water at 20℃; for 5h;	63.3%
With potassium carbonate In tetrahydrofuran; water

: 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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Stage #1: 3-({2-[(4-carbamimidoyl-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-ylamino)propionic acid ethyl ester hydrochloride With potassium carbonate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: n-hexyl chloroformate In tetrahydrofuran at 20℃; for 1h; Further stages.;	51%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;

: 82357-48-0
4-methylamino-3-nitro-benzoic acid chloride

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: Et3N / tetrahydrofuran / 20 °C 2.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 3.1: CDI / tetrahydrofuran / 50 °C 3.2: tetrahydrofuran / 24 h / Heating 4.1: glacial acetic acid / 1 h / Heating 5.1: HCl / ethanol / 0 °C 5.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 6.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 6.2: 51 percent / tetrahydrofuran / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: Et3N / tetrahydrofuran / 20 °C
2.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C
3.1: CDI / tetrahydrofuran / 50 °C
3.2: tetrahydrofuran / 24 h / Heating
4.1: glacial acetic acid / 1 h / Heating
5.1: HCl / ethanol / 0 °C
5.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C
6.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C
6.2: 51 percent / tetrahydrofuran / 1 h / 20 °C
View Scheme

: 41263-74-5
4-(methylamino)-3-nitrobenzoic acid

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: SOCl2 / dimethylformamide / 0.5 h / Heating 2.1: Et3N / tetrahydrofuran / 20 °C 3.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 4.1: CDI / tetrahydrofuran / 50 °C 4.2: tetrahydrofuran / 24 h / Heating 5.1: glacial acetic acid / 1 h / Heating 6.1: HCl / ethanol / 0 °C 6.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 7.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 7.2: 51 percent / tetrahydrofuran / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: SOCl2 / dimethylformamide / 0.5 h / Heating
2.1: Et3N / tetrahydrofuran / 20 °C
3.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C
4.1: CDI / tetrahydrofuran / 50 °C
4.2: tetrahydrofuran / 24 h / Heating
5.1: glacial acetic acid / 1 h / Heating
6.1: HCl / ethanol / 0 °C
6.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C
7.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C
7.2: 51 percent / tetrahydrofuran / 1 h / 20 °C
View Scheme

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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: CDI / tetrahydrofuran / 50 °C 1.2: tetrahydrofuran / 24 h / Heating 2.1: glacial acetic acid / 1 h / Heating 3.1: HCl / ethanol / 0 °C 3.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 4.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 4.2: 51 percent / tetrahydrofuran / 1 h / 20 °C View Scheme

: 429659-01-8
ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 65 percent / H2 / 10percent Pd/C / methanol / 20 °C 2.1: CDI / tetrahydrofuran / 50 °C 2.2: tetrahydrofuran / 24 h / Heating 3.1: glacial acetic acid / 1 h / Heating 4.1: HCl / ethanol / 0 °C 4.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 5.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 5.2: 51 percent / tetrahydrofuran / 1 h / 20 °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

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: HCl / ethanol / 0 °C 1.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 2.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 2.2: 51 percent / tetrahydrofuran / 1 h / 20 °C View Scheme

: 948551-71-1
3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: glacial acetic acid / 1 h / Heating 2.1: HCl / ethanol / 0 °C 2.2: 71 percent / (NH4)2CO3 / ethanol / 20 °C 3.1: aq. K2CO3 / tetrahydrofuran / 0.25 h / 20 °C 3.2: 51 percent / tetrahydrofuran / 1 h / 20 °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

: 6092-54-2
n-hexyl chloroformate

: 211915-06-9
dabigatran etexilate

Conditions

Conditions	Yield
Alkaline conditions;
Stage #1: 1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt With potassium carbonate In water; acetonitrile at 27℃; for 0.5h; Stage #2: n-hexyl chloroformate In water; acetonitrile at 12 - 20℃; for 2h;	16.4 g

: 75-75-2
methanesulfonic acid

: 211915-06-9
dabigatran etexilate

: 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridine-2-yl-amino]propionic acid ethyl ester methane sulphonate hemihydrate

Conditions

Conditions	Yield
With water In ethanol; ethyl acetate at 35 - 40℃; for 1h;	99%

: 75-75-2
methanesulfonic acid

: 211915-06-9
dabigatran etexilate

: ethyl N-{[2-({[4-((E)-amino{[(hexyloxy)carbonyl]imino}methyl)phenyl]amino}methyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-β-alaninate methanesulfonate

Conditions

Conditions	Yield
In acetone at 0 - 46℃; for 0.916667 - 2h;	90%
In acetone at 20 - 45℃; for 0.916667 - 1.66667h; Product distribution / selectivity;	90%

: 211915-06-9
dabigatran etexilate

: 1415506-19-2, 212321-78-3
3-({2-[(4-{amino-[(E)-hexyloxycarbonylimino]methyl}-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 5h;	77.5%
With sodium hydroxide In ethanol; water
With water; sodium hydroxide In ethanol

: 211915-06-9
dabigatran etexilate

: 1415901-76-6, 1416446-28-0
C40H47N9O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 5 h / 20 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 10.5 h / 0 - 20 °C View Scheme

: 211915-06-9
dabigatran etexilate

: ethyl N-{[2-({[4-((E)-amino{[(hexyloxy)carbonyl]imino}methyl)phenyl]-amino}methyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-β-alaninate nitrate salt

Conditions

Conditions	Yield
With nitric acid In acetone at 10 - 32℃; for 1h;	5 g

: 331-39-5
caffeic acid

: 211915-06-9
dabigatran etexilate

: ethyl N-{[2-({[4-((E)-amino{[(hexyloxy)carbonyl]imino}methyl)phenyl]-amino}methyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-β-alaninate caffeic acid salt

Conditions

Conditions	Yield
In acetone at 10 - 45℃; for 2.5h;	4.7 g

: 149-91-7
3,4,5-trihydroxybenzoic acid

: 211915-06-9
dabigatran etexilate

: ethyl N-{[2-({[4-((E)-amino{[(hexyloxy)carbonyl]imino}methyl)phenyl]-amino}methyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-β-alaninate gallic acid salt

Conditions

Conditions	Yield
In acetone at 0 - 35℃; for 5.25h;	4.7 g

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 211915-06-9
dabigatran etexilate

: ethyl N-{[2-({[4-((E)-amino{[(hexyloxy)carbonyl]imino}methyl)phenyl]-amino}methyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-β-alaninate bisferulate salt

Conditions

Conditions	Yield
In acetone at 1 - 42℃; for 3h; Temperature;	5.5 g

Dabigatran etexilate Chemical Properties

Molecular Structure of Dabigatran etexilate (CAS NO.211915-06-9):

IUPAC Name: ethyl 3-[[2-[[4-[(E)-N'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate
Empirical Formula: C₃₄H₄₁N₇O₅
Molecular Weight: 627.7332
H bond acceptors: 12
H bond donors: 3
Freely Rotating Bonds: 18
Polar Surface Area: 122.46 Å²
Index of Refraction: 1.614
Molar Refractivity: 175.87 cm³
Molar Volume: 504 cm³
Surface Tension: 49.2 dyne/cm
Density: 1.24 g/cm³
Flash Point: 454.5 °C
Enthalpy of Vaporization: 120.31 kJ/mol
Boiling Point: 827.9 °C at 760 mmHg
Vapour Pressure: 1.49E-27 mmHg at 25°C
Smiles
c1(ccc(NCc2n(c3c(n2)cc(cc3)C(=O)N(c2ncccc2)CCC(=O)OCC)C)cc1)\C(N)=N/C(=O)OCCCCCC

Dabigatran etexilate Specification

Dabigatran etexilate , with CAS number of 211915-06-9, can be called Ethyl 3-(((2-(((4-((((hexyloxy)carbonyl)amino)iminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)(pyridin-2-yl)amino)propanoate ; Pradax ; beta-Alanine, N-((2-(((4-((((hexyloxy)carbonyl)amino)iminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-, ethyl ester .

Product Name

Dabigatran etexilate

Synthetic route

Dabigatran etexilate Chemical Properties

Dabigatran etexilate Specification

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