[ CAS No. 211914-51-1 ] {[proInfo.proName]}

Name: 211914-51-1|3-(2-(((4-Carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoic acid|98%
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Quality Control of [ 211914-51-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 211914-51-1 ]

CAS No. :	211914-51-1	MDL No. :	MFCD09837830
Formula :	C₂₅H₂₅N₇O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YBSJFWOBGCMAKL-UHFFFAOYSA-N
M.W :	471.51	Pubchem ID :	216210
Synonyms :	BIBR 953;BIBR 953ZW	Chemical Name :	3-(2-(((4-Carbamimidoylphenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoic acid

Safety of [ 211914-51-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 211914-51-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 211914-51-1 ]

[ 211914-51-1 ] Synthesis Path-Downstream 1~30

1
[ 211914-50-0 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide In ethanol at 20℃; for 2h;
91%	With sodium hydroxide	59 1-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-hydroxycarbonylethyl)-amide EXAMPLE 59 1-Methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-hydroxycarbonylethyl)-amide Prepared analogously to Example 26 from 1-methyl-2-[N-(4-amidinophenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide-hydrochloride and sodium hydroxide solution. Yield: 91% of theory, C25 H25 N7 O3 (471.5) EQU37

Reference： [1]Hauel, Norbert H.; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean-Marie; Wienen, Wolfgang [Journal of Medicinal Chemistry, 2002, vol. 45, # 9, p. 1757 - 1766]
[2]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US6087380, 2000, A

2
[ 82357-48-0 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	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: 91 percent / aq. NaOH / ethanol / 2 h / 20 °C
	Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 12 h / 20 °C 2.1: 10% Pd/C / 20 h / 22801.5 Torr 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 3.2: 20 °C 4.1: hydrogenchloride / ethanol / 12 h / 20 °C 4.2: 5 h / 20 °C 5.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

Reference： [1]Hauel, Norbert H.; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean-Marie; Wienen, Wolfgang [Journal of Medicinal Chemistry, 2002, vol. 45, # 9, p. 1757 - 1766]
[2]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

3
[ 41263-74-5 ]
dabigatran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1757 - 1766
[2]Patent: CN103524559,2016,B

4
[ 212322-56-0 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	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: 91 percent / aq. NaOH / ethanol / 2 h / 20 °C
	Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 1.2: 20 °C 2.1: hydrogenchloride / ethanol / 12 h / 20 °C 2.2: 5 h / 20 °C 3.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

Reference： [1]Hauel, Norbert H.; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean-Marie; Wienen, Wolfgang [Journal of Medicinal Chemistry, 2002, vol. 45, # 9, p. 1757 - 1766]
[2]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

5
[ 429659-01-8 ]
dabigatran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	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: 91 percent / aq. NaOH / ethanol / 2 h / 20 °C
	Multi-step reaction with 4 steps 1.1: palladium 10% on activated carbon / 20 h / 22801.5 Torr 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 2.2: 20 °C 3.1: hydrogenchloride / ethanol / 12 h / 20 °C 3.2: 5 h / 20 °C 4.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

Reference： [1]Hauel, Norbert H.; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean-Marie; Wienen, Wolfgang [Journal of Medicinal Chemistry, 2002, vol. 45, # 9, p. 1757 - 1766]
[2]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

6
[ 211915-84-3 ]
dabigatran [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1757 - 1766
[2]Patent: CN103524559,2016,B
[3]Patent: CN104177337,2019,B

7
[ 948551-71-1 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	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: 91 percent / aq. NaOH / ethanol / 2 h / 20 °C

Reference： [1]Hauel, Norbert H.; Nar, Herbert; Priepke, Henning; Ries, Uwe; Stassen, Jean-Marie; Wienen, Wolfgang [Journal of Medicinal Chemistry, 2002, vol. 45, # 9, p. 1757 - 1766]

8
[ 22128-62-7 ]
[ 211914-51-1 ]
[ 1943762-51-3 ]

Yield	Reaction Conditions	Operation in experiment
71.9%	With 4-methyl-morpholine In chloroform at 0 - 20℃; for 25h;	1.1 Chloromethyl chloroformate (0.27 g, 2.12 mmol) was added dropwise to a solution of dabigatran (1.0 g, 2.12 mmol) and N-methylmorpholine (0.2 ml) in chloroform (10 ml), and the mixture was stirred at 0 ° C for 1 hour, and then allowed to react at room temperature for 24 hours.Washed with saturated brine (10 mL x 3), dried over anhydrous sodium sulfate,The filtrate was concentrated to dryness and the residue was purified by column chromatography to give 10.86 g of a light yellow solid II as a 71.9%

Reference： [1]Current Patent Assignee: SHENYANG UNIVERSITY OF TECHNOLOGY - CN105646531, 2016, A Location in patent: Paragraph 0054; 0055

9
[ 211914-51-1 ]
[ 1943762-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 4-methyl-morpholine / chloroform / 25 h / 0 - 20 °C 2: sodium iodide / acetone / 24 h / Reflux 3: caesium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C

Reference： [1]Current Patent Assignee: SHENYANG UNIVERSITY OF TECHNOLOGY - CN105646531, 2016, A

10
[ 211914-51-1 ]
[ 1943762-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 4-methyl-morpholine / chloroform / 25 h / 0 - 20 °C 2: sodium iodide / acetone / 24 h / Reflux

Reference： [1]Current Patent Assignee: SHENYANG UNIVERSITY OF TECHNOLOGY - CN105646531, 2016, A

11
[ 429658-95-7 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium hydroxide In ethanol at 20℃; for 3h;	1.9 Synthesis of 3-(1-methyl-2-(4-amidino-phenylaminomethyl)benzotriazol-5-ylcarboxylic acid-(N-2-pyridyl)amido)propionic acid 3-(1-Methyl-2- (4-amidino-phenylaminomethyl) -benzoimidazol-5-yl- carboxylic acid-(N-2-pyridyl) amido) propanoic acidEthyl ester(8.0 g, 16 mmol) was dissolved in 160 ml absolute ethanol 80 ml H20, sodium hydroxide (1.92 g, 48 mmol) was added, stirred at room temperature for 3 h, diluted with 400 ml water, neutralized with appropriate amount of acetic acid, The white precipitate was precipitated and the solution was filtered off and washed successively with water, absolute ethanol and anhydrous ethyl ether to give 3- (1-methyl-2- (4-amidino-phenylaminomethyl) 5-yl-carboxylic acid- (N-2-pyridyl) amido) propionic acid (6.3 g, yield 84%). Mass spectrum (ESI-MS): 472 • 1 (M + H) +, 494.2 (M + Na) +; C25H25N7O3 (471)

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B Location in patent: Paragraph 0096; 0123-0125

12
[ 211914-51-1 ]
[ 1546349-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C 2.1: potassium hydroxide / water; tetrahydrofuran / 0.25 h / 20 °C 2.2: 2 h

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

13
[ 3476-44-6 ]
[ 211914-51-1 ]
[ 1546350-00-8 ]

Yield	Reaction Conditions	Operation in experiment
73.4%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	1.10 Synthesis of 3-(1-methyl-2-(4-amidinophenylaminomethyl)-benzoimidazol-5-yl-carboxylic acid)-(N-2-pyridyl) Acid-2-(n-heptadecylcarbonyloxy)glycerophosphorylcholine-3-yl-ester To a dry 100mL round bottom flask was added dichloromethane 30 ~ 40ml, 3- (l-methyl-2- (4-amidino-phenylaminomethyl) (N-2-pyridyl) amido) propionic acid, 5.6 g of 2- (n-heptadecylcarbonyloxy) glycerophosphorylcholine, 0.15 g of dicyclohexylcarbodiimide , 4 - 1 1 dimethylaminopyridine (01 ^?) 701 ^, stirred at room temperature for 3h (TLC test endpoint), the reaction was complete suction filtration, the filtrate was washed with 3 X 20mL20% sodium carbonate solution, and then with The saturated sodium chloride solution was washed until neutral, dried over anhydrous magnesium sulfate and the solvent was evaporated to give a yellow solid which was recrystallized from 95% ethanol to give 3- (1-methyl-2- (4-amidine (N-2-pyridyl) -amino-propionic acid-2_ (n-heptadecylcarbonyloxy) glyceryl phosphorylcholine (ESI): 977.4 (M + H) +, 999.5 (M + Na) +; C5iH77N8O9P (976)

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B Location in patent: Paragraph 0096; 0126-0128

14
[ 504-29-0 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 24 h / 100 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 12 h / 20 °C 3.1: 10% Pd/C / 20 h / 22801.5 Torr 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 4.2: 20 °C 5.1: hydrogenchloride / ethanol / 12 h / 20 °C 5.2: 5 h / 20 °C 6.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

15
[ 103041-38-9 ]
dabigatran [ No CAS ]

Reference： [1]Patent: CN103524559,2016,B

16
[ 873-74-5 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: water / Reflux 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 2.2: 20 °C 3.1: hydrogenchloride / ethanol / 12 h / 20 °C 3.2: 5 h / 20 °C 4.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

17
[ 42288-26-6 ]
dabigatran [ No CAS ]

Reference： [1]Patent: CN103524559,2016,B

18
[ 96-99-1 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: vaseline / 100 °C 2.1: thionyl chloride / 1.5 h / Reflux 3.1: triethylamine / dichloromethane / 12 h / 20 °C 4.1: 10% Pd/C / 20 h / 22801.5 Torr 5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.75 h / 0 °C 5.2: 20 °C 6.1: hydrogenchloride / ethanol / 12 h / 20 °C 6.2: 5 h / 20 °C 7.1: sodium hydroxide; water / ethanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN103524559, 2016, B

19
[ CAS Unavailable ]
[ 211914-51-1 ]
[ CAS Unavailable ]

Reference： [1]Current Patent Assignee: WUHAN ZHONGYOU PHARMACEUTICAL; QR PHARMACEUTICALS; SHANGHAI MEIYUE BIOTECHNOLOGY DEV - CN107739384, 2018, A Location in patent: Paragraph 0007

20
[ 541-41-3 ]
[ 211914-51-1 ]
[ 2194578-56-6 ]

Yield	Reaction Conditions	Operation in experiment
79.2%	Stage #1: dabigatran With chloro-trimethyl-silane In dichloromethane at 60℃; for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 60℃; for 0.5h; Stage #3: chloroformic acid ethyl ester In dichloromethane at 20℃; for 0.666667h; Cooling with ice;	1 Example 1 Preparation of Compound of Formula IIa Trimethylchlorosilane (92 mg, 0.84 mmol) dissolved in 0.5 ml of anhydrous dichloromethane was slowly added dropwise at room temperature to the compound of formula I (100 mg) dissolved in 2 ml of anhydrous dichloromethane. In a 0.21 mmol) system, the reaction was then warmed to 60°C and stirred for approximately 30 minutes. After cooling to room temperature, 0.5 mL of anhydrous dichloromethane in N,N-diisopropylethylamine (136 mg, 1.06 mmol) was dissolved. ) was added dropwise to the reaction solution, warmed to 60 degrees for 30 minutes, and then cooled to room temperature.Ethyl chloroformate (120 mg, 0.84 mmol) dissolved in 0.5 mL of anhydrous methylene chloride was slowly added dropwise to the reaction solution under ice cooling, and the mixed solution was stirred in an ice bath for 40 minutes. 1 drop of water was quenched, the organic phase was separated, and concentrated under reduced pressure to give a yellow solid, which was a compound of formula IIa, weight 96 mg, yield 79.2%,

Reference： [1]Current Patent Assignee: WUHAN ZHONGYOU PHARMACEUTICAL; QR PHARMACEUTICALS; SHANGHAI MEIYUE BIOTECHNOLOGY DEV - CN107739384, 2018, A Location in patent: Paragraph 0012

21
[ 211914-51-1 ]
[ 1936413-83-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride In water at 20 - 40℃; for 0.166667h;	1 comparative example 1 preparation of formula V compound [3-(2-(((4-methylamidinophenyl)amino)methyl)-1-methyl-N-(pyridine-2-yl)-1H-benzo[d]imidazole-5- carbonylamino)propionic acid hydrochloride] 0.25 mL of 1 Μ HCl was added dropwise to a 20 mL aqueous solution of the compound of formula IV (dabigatran, 118 mg, 0.25 mmol) at room temperature, and the reaction solution was stirred at 40 ° C for 10 min, and the reaction mixture became cloudy. Then, 20 mL of methanol was slowly added until the reaction system was clarified, and the reaction liquid was concentrated under reduced pressure and lyophilized to give a white solid 124 mg(formula V). Yield 98%

Reference： [1]Current Patent Assignee: SHANGHAI MEIYUE BIOTECHNOLOGY DEV - CN109125274, 2019, A Location in patent: Paragraph 0073-0078

22
[ 67-63-0 ]
[ 211914-51-1 ]
[ 1610758-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride at 20℃;	13.1 Synthesis of Compound 27 Compound I-1 (400 mg, 0.85 mmol) and thionyl chloride (0.5 mL) were added to an isopropyl alcohol solution (6 mL), and stirred at room temperature overnight. The mixture was concentrated to dryness under reduced pressure.The white solid compound 27 was obtained and used directly in the next step.

Reference： [1]Current Patent Assignee: SHANGHAI MEIYUE BIO TECH DEV; SHANGHAI MEIYUE BIOTECHNOLOGY DEV - CN109897028, 2019, A Location in patent: Paragraph 0293; 0296-0297

23
[ 211914-51-1 ]
[ 2347485-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / 20 °C 2.1: N,N-dimethyl-formamide / 2 h / 45 °C 2.2: 35 °C

Reference： [1]Current Patent Assignee: SHANGHAI MEIYUE BIO TECH DEV; SHANGHAI MEIYUE BIOTECHNOLOGY DEV - CN109897028, 2019, A

24
[ 1466608-48-9 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water for 6h;	14 Preparation of dabigatran (II) and crystal form A 4.5 g (7.5 mmol) of hydrazine methanesulfonate (III-2) was added to 60 mL of ethanol.1.2 g (30 mmol) of sodium hydroxide was added dropwise with stirring.Aqueous solution 150mL,After the completion of the dropwise addition, stirring was continued for 6 hours, filtration, and the filter cake was washed with water.Drying under vacuum at 40 to 50 ° C gives the crystalline form A of dabigatran (II).HPLC purity: 99.0%

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN104177337, 2019, B Location in patent: Paragraph 0231-0242

25
[ 1639946-98-7 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate / water / 20 - 25 °C / pH Ca_. 10 1.2: 8 h 2.1: sodium hydroxide / water; ethanol / 6 h

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN104177337, 2019, B

26
[ 1354892-78-6 ]
[ 211914-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: acetone / 2 h / 20 °C 2.1: potassium carbonate / water / 20 - 25 °C / pH Ca_. 10 2.2: 8 h 3.1: sodium hydroxide / water; ethanol / 6 h

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - CN104177337, 2019, B

27
[ 211914-51-1 ]
[ 2625409-80-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h 2: hydrogenchloride / acetonitrile; water; 1,4-dioxane / 0.5 h / 20 °C 3: triethylamine / N,N-dimethyl-formamide / 4 h

Reference： [1]Current Patent Assignee: AUBURN UNIVERSITY; MASS GENERAL BRIGHAM INC - WO2022/6007, 2022, A1

28
[ 211914-51-1 ]
[ 2625409-78-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h 2: hydrogenchloride / acetonitrile; water; 1,4-dioxane / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: AUBURN UNIVERSITY; MASS GENERAL BRIGHAM INC - WO2022/6007, 2022, A1

29
[ 211914-51-1 ]
[ 2625409-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h 2: hydrogenchloride / acetonitrile; water; 1,4-dioxane / 0.5 h / 20 °C 3: triethylamine / acetonitrile / 0.08 h / 65 °C

Reference： [1]Current Patent Assignee: AUBURN UNIVERSITY; MASS GENERAL BRIGHAM INC - WO2022/6007, 2022, A1

30
[ 153086-78-3 ]
[ 211914-51-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
67.2%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 3h;	Synthesizing dabigatran-NH2: dabigatran (50 mg, 106 μmol) was suspended in dimethylformamide (DMF, 4.0 mL) in a 20-mL vial with a magnetic stir-bar, to which N-Boc- 2,2′-(ethylenedioxy)diethylamine (105 mg, 424 μmol) and EDC (265 mg, 1.38 mmol) were then added. After stirring for 3 h, the reaction mixture was concentrated to dryness, re-dissolved in DMSO:H2O (2.0:0.1 mL) and subjected to reverse phase chromatography, resulting in 50 mg for a 67.2 % isolated yield of Dabigatran-NH-Boc. LC-ESI-MS(+) m/z = 702.5 [M+H+]+. Dabigatran-NH-Boc was dissolved in H2O:MeCN (1:1, 400 μL), and then HCl (4 M) in dioxane (1 mL) was added. The homogeneous solution was stirred at room temperature for 30 min and the reaction was concentrated by rotovap to give 41 mg, a 95.6 % yield, of Dabigatran- NH2 as a colorless solid. LC-ESI-MS(+) m/z = 602.4 [M+H+]+; LC-ESI-MS(-) m/z = 600.4 [M-H+]-.
67.2%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 3h;	Synthesizing dabigatran-NH2: dabigatran (50 mg, 106 μmol) was suspended in dimethylformamide (DMF, 4.0 mL) in a 20-mL vial with a magnetic stir-bar, to which N-Boc- 2,2′-(ethylenedioxy)diethylamine (105 mg, 424 μmol) and EDC (265 mg, 1.38 mmol) were then added. After stirring for 3 h, the reaction mixture was concentrated to dryness, re-dissolved in DMSO:H2O (2.0:0.1 mL) and subjected to reverse phase chromatography, resulting in 50 mg for a 67.2 % isolated yield of Dabigatran-NH-Boc. LC-ESI-MS(+) m/z = 702.5 [M+H+]+. Dabigatran-NH-Boc was dissolved in H2O:MeCN (1:1, 400 μL), and then HCl (4 M) in dioxane (1 mL) was added. The homogeneous solution was stirred at room temperature for 30 min and the reaction was concentrated by rotovap to give 41 mg, a 95.6 % yield, of Dabigatran- NH2 as a colorless solid. LC-ESI-MS(+) m/z = 602.4 [M+H+]+; LC-ESI-MS(-) m/z = 600.4 [M-H+]-.

Reference： [1]Current Patent Assignee: AUBURN UNIVERSITY; MASS GENERAL BRIGHAM INC - WO2022/6007, 2022, A1 Location in patent: Page/Page column 4; 45
[2]Current Patent Assignee: AUBURN UNIVERSITY; MASS GENERAL BRIGHAM INC - WO2022/6007, 2022, A1 Location in patent: Page/Page column 4; 45

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P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 211914-51-1 ] {[proInfo.proName]}

Quality Control of [ 211914-51-1 ]

Related Doc. of [ 211914-51-1 ]

Product Details of [ 211914-51-1 ]

Safety of [ 211914-51-1 ]

Application In Synthesis of [ 211914-51-1 ]

[ 211914-51-1 ] Synthesis Path-Downstream 1~30

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry