Product Name

  • Name

    N-[2]PYRIDYL-B-ALANIN-ETHYL ESTER

  • EINECS -0
  • CAS No. 103041-38-9
  • Article Data11
  • CAS DataBase
  • Density 1.132 g/cm3
  • Solubility
  • Melting Point 48-50°C
  • Formula C10H14N2O2
  • Boiling Point 337.812 °C at 760 mmHg
  • Molecular Weight 194.233
  • Flash Point 158.103 °C
  • Transport Information
  • Appearance off-white crystals
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 103041-38-9 (N-[2]PYRIDYL-B-ALANIN-ETHYL ESTER)
  • Hazard Symbols
  • Synonyms b-Alanine, N-2-pyridyl-, ethylester (6CI);
  • PSA 51.22000
  • LogP 1.51970

Synthetic route

2-aminopyridine
504-29-0

2-aminopyridine

ethyl acrylate
140-88-5

ethyl acrylate

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In ethanol at 120℃; for 12h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Green chemistry; chemoselective reaction;94%
With acetic acid In acetic acid at 88℃; Product distribution / selectivity;86.7%
In acetic acid at 88℃; Product distribution / selectivity;86.7%
ethanol
64-17-5

ethanol

3-[(pyridin-2-yl)amino]propanoic acid
104961-64-0

3-[(pyridin-2-yl)amino]propanoic acid

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

Conditions
ConditionsYield
With thionyl chloride at 0 - 70℃; for 12h;69.2%
2-aminopyridine
504-29-0

2-aminopyridine

4-tert-Butylcatechol
98-29-3

4-tert-Butylcatechol

ethyl acrylate
140-88-5

ethyl acrylate

A

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

B

3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one
5439-14-5

3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one

...Expand
2-aminopyridine
504-29-0

2-aminopyridine

ethyl acrylate
140-88-5

ethyl acrylate

A

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

B

3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one
5439-14-5

3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one

...Expand
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

2-(chloromethyl)-1-methyl-1H-benzimidazole-6-carboxylic acid

2-(chloromethyl)-1-methyl-1H-benzimidazole-6-carboxylic acid

ethyl 3-(2-(chloromethyl)-1-methyl-N-(pyridin-2-yl)-1H-benzimidazole-6-carboxamido)propanate

ethyl 3-(2-(chloromethyl)-1-methyl-N-(pyridin-2-yl)-1H-benzimidazole-6-carboxamido)propanate

Conditions
ConditionsYield
With triethylamine In ethyl acetate at -10℃; Reagent/catalyst; Temperature; Solvent;97.7%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

3-Bromo-4-ethylbenzoic acid
99548-53-5

3-Bromo-4-ethylbenzoic acid

C18H20BrN3O3

C18H20BrN3O3

Conditions
ConditionsYield
Stage #1: 3-Bromo-4-ethylbenzoic acid With thionyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at -20 - 20℃; for 5h;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With pyridine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 6h; Solvent; Reagent/catalyst;		97%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-(methylamino)-3-nitrobenzoic acid

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride
1187067-68-0

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Solvent; Reagent/catalyst;95.2%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

4-chloro-3-nitro-benzoyl chloride
38818-50-7

4-chloro-3-nitro-benzoyl chloride

3-[(4-chloro-3-nitrobenzoyl)pyridin-2-yl-amino]propionic acid ethyl ester
1620205-04-0

3-[(4-chloro-3-nitrobenzoyl)pyridin-2-yl-amino]propionic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h; Solvent; Reagent/catalyst;87%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃; for 1h;
With triethylamine In dichloromethane at 20℃; for 1h; Solvent; Reagent/catalyst;16.3 g
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

4-methylamino-3-nitrobenzoyl chloride hydrochloride

4-methylamino-3-nitrobenzoyl chloride hydrochloride

ethyl 3-[((4-methylamino-3-nitrobenzoyl)pyridin-2-yl)amino]propanoate

ethyl 3-[((4-methylamino-3-nitrobenzoyl)pyridin-2-yl)amino]propanoate

Conditions
ConditionsYield
Stage #1: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate; 4-methylamino-3-nitrobenzoyl chloride hydrochloride With triethylamine In toluene at 0 - 30℃; for 3h; Large scale;
Stage #2: In ethanol; toluene at 20 - 70℃; Large scale;		87%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

C10H8Cl2N2O

C10H8Cl2N2O

N-[[2-(chloromethyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridyl-β-alanine ethyl ester
1307233-94-8

N-[[2-(chloromethyl)-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridyl-β-alanine ethyl ester

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 1h;85%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

ethyl 3-(methyl(pyridin-2-yl)amino)propanoate

ethyl 3-(methyl(pyridin-2-yl)amino)propanoate

Conditions
ConditionsYield
Stage #1: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With formaldehyd; acetic acid In methanol; water at 30℃; for 2h; Inert atmosphere;
Stage #2: With sodium cyanoborohydride In methanol; water at 0 - 30℃; Inert atmosphere;		84%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

2-[((4-[([(hexyloxy)carbonyl]amino)methanimidoyl]phenyl)amino)methyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester

2-[((4-[([(hexyloxy)carbonyl]amino)methanimidoyl]phenyl)amino)methyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester

dabigatran etexilate
211915-06-9

dabigatran etexilate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; for 7h;82.6%
methyl-3-methoxy-4-(methylamino)benzoate

methyl-3-methoxy-4-(methylamino)benzoate

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

C19H23N3O4

C19H23N3O4

Conditions
ConditionsYield
In ethyl acetate at 25℃; for 12h; Temperature; Concentration;80.7%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

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

Conditions
ConditionsYield
With thionyl chloride; triethylamine In dichloromethane80%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

2-[((4-[([(hexyloxy)carbonyl]amino)methanimidoyl]phenyl)amino)methyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

2-[((4-[([(hexyloxy)carbonyl]amino)methanimidoyl]phenyl)amino)methyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

dabigatran etexilate
211915-06-9

dabigatran etexilate

Conditions
ConditionsYield
Stage #1: 2-[((4-[([(hexyloxy)carbonyl]amino)methanimidoyl]phenyl)amino)methyl]-1-methyl-1H-benzimidazole-5-carboxylic acid With thionyl chloride In tetrahydrofuran for 2h; Reflux;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 5h;		75.6%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-(methylamino)-3-nitrobenzoic acid

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride

Conditions
ConditionsYield
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide for 0.75h; Reflux;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In tetrahydrofuran at 20 - 60℃;
Stage #3: With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;		47.2%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-(methylamino)-3-nitrobenzoic acid

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride

ethyl 3-{[{1-(methylamino)-2-nitrophen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate hydrochloride

Conditions
ConditionsYield
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide for 0.75h; Reflux;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In tetrahydrofuran at 20 - 60℃;
Stage #3: With hydrogenchloride In ethyl acetate Product distribution / selectivity;		47.2%
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-methylamino-3-nitro-benzoic acid chloride

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

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

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;
Stage #1: 4-methylamino-3-nitro-benzoic acid chloride With triethylamine In dichloromethane at 0 - 10℃;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate In dichloromethane at 0 - 30℃;		180 g
With triethylamine In dichloromethane at 20℃; for 12h;
With triethylamine In dichloromethane at 0 - 5℃; Inert atmosphere;
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-methylamino-3-nitro-benzoic acid chloride

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride
1187067-68-0

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride

Conditions
ConditionsYield
Stage #1: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate; 4-methylamino-3-nitro-benzoic acid chloride With triethylamine In tetrahydrofuran at 30 - 40℃; for 2.25h;
Stage #2: With hydrogenchloride In diethyl ether; ethyl acetate
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-methylamino-3-nitro-benzoic acid chloride

ethyl N-(4-methylamine-3-nitrobenzoyl)-N-(2-pyridyl)-3-aminopropionate hydrobromide

ethyl N-(4-methylamine-3-nitrobenzoyl)-N-(2-pyridyl)-3-aminopropionate hydrobromide

Conditions
ConditionsYield
Stage #1: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate; 4-methylamino-3-nitro-benzoic acid chloride With triethylamine In tetrahydrofuran at 0 - 20℃;
Stage #2: With hydrogen bromide In tetrahydrofuran at 0 - 20℃; for 1.5h; Product distribution / selectivity;
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0.75 h / Reflux
1.2: 20 - 60 °C
2.1: ammonium formate / palladium on activated charcoal / ethanol / 3 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Reflux
3.2: 10 h / Reflux
4.1: hydrogenchloride; toluene-4-sulfonic acid / ethanol / 48 h / 20 °C
4.2: 10 - 20 °C
4.3: 0.75 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 0 - 10 °C
1.2: 0 - 30 °C
2.1: hydrogen / ethyl acetate / 60 - 65 °C / 7500.75 Torr
3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 5 °C
3.2: 0.08 h / 0 - 5 °C
4.1: ammonium hydroxide / water; dichloromethane / pH 8 - 10
5.1: hydrogenchloride / ethanol / 35 - 42 °C
5.2: 0 - 32 °C
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 12 h / 20 °C
2.1: palladium 10% on activated carbon / 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
View Scheme
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

dabigatran etexilate
211915-06-9

dabigatran etexilate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0.75 h / Reflux
1.2: 20 - 60 °C
2.1: ammonium formate / palladium on activated charcoal / ethanol / 3 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Reflux
3.2: 10 h / Reflux
4.1: hydrogenchloride; toluene-4-sulfonic acid / ethanol / 48 h / 20 °C
4.2: 10 - 20 °C
4.3: 0.75 h / 50 °C
5.1: potassium carbonate / water; tetrahydrofuran / 0.25 h / 20 °C
5.2: 1 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2 h / 65 - 75 °C
1.2: 3 h / 20 - 30 °C
2.1: iron; hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3 h / 25 - 35 °C
3.2: 24 h / 25 - 35 °C
3.3: 3 h / 0 - 10 °C
4.1: calcium chloride; hydrogenchloride / ethanol / 13 h / -15 - 35 °C
4.2: 23.66 h / -35 - 30 °C
5.1: dichloromethane / 3 h / 15 - 25 °C
5.2: 8 h / 25 - 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: triethylamine / dichloromethane / 0 - 10 °C
1.2: 0 - 30 °C
2.1: hydrogen / ethyl acetate / 60 - 65 °C / 7500.75 Torr
3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 5 °C
3.2: 0.08 h / 0 - 5 °C
4.1: ammonium hydroxide / water; dichloromethane / pH 8 - 10
5.1: hydrogenchloride / ethanol / 35 - 42 °C
5.2: 0 - 32 °C
6.1: potassium carbonate / water; acetonitrile / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: ammonium chloride / water / 80 - 90 °C
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux
3.2: 20 h / Inert atmosphere; Reflux
4.1: sodium hydroxide; potassium iodide; sodium carbonate / dichloromethane; water / 3 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: ammonium chloride / water / 80 - 90 °C
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux
3.2: 20 h / Inert atmosphere; Reflux
4.1: sodium hydroxide; potassium iodide; sodium hydrogencarbonate / water; ethyl acetate / 2 h / 40 °C
View Scheme
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

ethyl 3-[[[-2-[[(4-cyanophenyl)amino]phenyl]-1-methyl-1H-benzoimidazol-5-yl]carbonyl]pyridine-2-ylamino]propionate oxalate
1223061-77-5

ethyl 3-[[[-2-[[(4-cyanophenyl)amino]phenyl]-1-methyl-1H-benzoimidazol-5-yl]carbonyl]pyridine-2-ylamino]propionate oxalate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0.75 h / Reflux
1.2: 20 - 60 °C
2.1: ammonium formate / palladium on activated charcoal / ethanol / 3 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Reflux
3.2: 10 h / Reflux
View Scheme
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl] amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-β-alanine ethyl ester methanesulfonate
872728-81-9

N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl] amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-β-alanine ethyl ester methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0.75 h / Reflux
1.2: 20 - 60 °C
2.1: ammonium formate / palladium on activated charcoal / ethanol / 3 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Reflux
3.2: 10 h / Reflux
4.1: hydrogenchloride; toluene-4-sulfonic acid / ethanol / 48 h / 20 °C
4.2: 10 - 20 °C
4.3: 0.75 h / 50 °C
5.1: potassium carbonate / water; acetone / 0.5 h / 5 °C
5.2: 1 h / 50 °C
5.3: 1 h / Reflux
View Scheme
Multi-step reaction with 6 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0.75 h / Reflux
1.2: 20 - 60 °C
2.1: ammonium formate / palladium on activated charcoal / ethanol / 3 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / Reflux
3.2: 10 h / Reflux
4.1: hydrogenchloride; toluene-4-sulfonic acid / ethanol / 48 h / 20 °C
4.2: 10 - 20 °C
4.3: 0.75 h / 50 °C
5.1: potassium carbonate / water; tetrahydrofuran / 0.25 h / 20 °C
5.2: 1 h / 20 °C
6.1: ethyl acetate / 2 h / 20 - 45 °C
View Scheme
Multi-step reaction with 6 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2 h / 65 - 75 °C
1.2: 3 h / 20 - 30 °C
2.1: iron; hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3 h / 25 - 35 °C
3.2: 24 h / 25 - 35 °C
3.3: 3 h / 0 - 10 °C
4.1: calcium chloride; hydrogenchloride / ethanol / 13 h / -15 - 35 °C
4.2: 23.66 h / -35 - 30 °C
5.1: dichloromethane / 3 h / 15 - 25 °C
5.2: 8 h / 25 - 50 °C
6.1: tetrahydrofuran / 5 h / 25 - 30 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: ammonium chloride / water / 80 - 90 °C
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux
3.2: 20 h / Inert atmosphere; Reflux
4.1: sodium hydroxide; potassium iodide; sodium carbonate / dichloromethane; water / 3 h / 50 °C
5.1: acetone / 3 h / 0 - 35 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2.1: ammonium chloride / water / 80 - 90 °C
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux
3.2: 20 h / Inert atmosphere; Reflux
4.1: sodium hydroxide; potassium iodide; sodium hydrogencarbonate / water; ethyl acetate / 2 h / 40 °C
5.1: acetone / 3 h / 0 - 35 °C
View Scheme
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / 0.75 h / Reflux
1.2: 20 - 60 °C
2.1: ammonium formate / palladium on activated charcoal / ethanol / 3 h / Reflux
View Scheme
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-methylamino-3-nitro-benzoic acid chloride

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride hemisulfate

ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]propanoate hydrochloride hemisulfate

Conditions
ConditionsYield
Stage #1: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate; 4-methylamino-3-nitro-benzoic acid chloride With triethylamine In tetrahydrofuran; dichloromethane at 40℃; for 2h;
Stage #2: With hydrogenchloride In chloroform
Stage #3: With sulfuric acid In dichloromethane
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

4-(methylamino)-3-nitrobenzoic acid

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

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

Conditions
ConditionsYield
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride In N,N-dimethyl-formamide at 25 - 80℃; for 1.25h;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In ethyl acetate; N,N-dimethyl-formamide for 1h;
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide at 25 - 80℃; for 1.4h;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In ethyl acetate for 1h;
Stage #1: 4-(methylamino)-3-nitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 65 - 75℃; for 2h;
Stage #2: 2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate With triethylamine In toluene at 20 - 30℃; for 3h;		162 g
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2 h / 65 - 75 °C
1.2: 3 h / 20 - 30 °C
2.1: iron; hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 0 - 10 °C
1.2: 0 - 30 °C
2.1: hydrogen / ethyl acetate / 60 - 65 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C
2: ammonium chloride / water / 80 - 90 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 12 h / 20 °C
2: palladium 10% on activated carbon / 20 h / 22801.5 Torr
View Scheme
2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate
103041-38-9

2-chloromethyl-1-methyl-1H-benzimidazole-5 ethyl acetate

ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate mesylate

ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate mesylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / toluene / 2 h / 65 - 75 °C
1.2: 3 h / 20 - 30 °C
2.1: iron; hydrogenchloride / tetrahydrofuran; water / 2 h / Reflux
3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3 h / 25 - 35 °C
3.2: 24 h / 25 - 35 °C
3.3: 3 h / 0 - 10 °C
View Scheme

Ethyl 3-(pyridin-2-ylamino)propanoate Chemical Properties

Product Name: Ethyl 3-(pyridin-2-ylamino)propanoate (CAS NO.103041-38-9)

Molecular Formula: C10H14N2O2
Molecular Weight: 194.23g/mol
Mol File: 103041-38-9.mol
Boiling point: 337.812 °C at 760 mmHg
Flash Point: 158.103 °C
Density: 1.132 g/cm3
Index of Refraction: 1.545 
Molar Refractivity: 54.26 cm3 
Molar Volume: 171.623 cm3 
Surface Tension: 44.869 dyne/cm
Enthalpy of Vaporization: 58.11 kJ/mol

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