10408-85-2

Usage

Uses

Used in Pharmaceutical Industry:
2,3-dihydro-1H-inden-2-yl(methyl)amine(HCl) is used as an intermediate for the synthesis of N-methyl-N-(2-propynyl)-1-indanamine, a potent monoamine oxidase inhibitor. Monoamine oxidase inhibitors are a class of drugs that are used to treat various psychiatric and neurological disorders, such as depression, anxiety, and Parkinson's disease. The compound's role in the synthesis of these inhibitors highlights its importance in the development of novel therapeutic agents for these conditions.

Synthetic route

tert-butyl (2,3-dihydro-1H-inden-2-yl)carbamate → N-methylindan-2-amine hydrochloride (10408-85-2)

Conditions	Yield
Stage #1: tert-butyl-2,3-dihydro-1H-inden-2-yl-carbamate With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether at 20℃;	3.53 g

2,3-dihydro-1H-inden-2-amine (2975-41-9) → N-methylindan-2-amine hydrochloride (10408-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 2.2: 20 °C View Scheme

N-[5-chloro-2-(4-chlorophenoxy)phenyl]iminodiacetic acid + N-methylindan-2-amine hydrochloride (10408-85-2) → N-[5-chloro-2-(4-chlorophenoxy)phenyl]-N-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}glycine

Conditions	Yield
Stage #1: N-[5-chloro-2-(4-chlorophenoxy)phenyl]iminodiacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-methylindan-2-amine hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 1h;	91%

(+/-)-3-(2-chloroethyl)-6-nitro-4-[3-(trifluoromethyl)benzoyl]-3,4-dihydro-2H-1,4-benzoxazine + N-methylindan-2-amine hydrochloride (10408-85-2) + (2E)-but-2-enedioic acid (110-17-8) → (+/-)-3-[2-[(2,3-Dihydro-1H-inden-2-yl)amino]ethyl]-6-nitro-4-[3-(trifluoromethyl)benzoyl]-3,4-dihydro-2H-1,4-benzoxazine (E)-2-butenedioate

Conditions	Yield
With potassium iodide; potassium carbonate In diethyl ether; water; N,N-dimethyl-formamide; isopropyl alcohol

(+/-)-3-(2-chloroethyl)-6-methoxy-4-[3-(trifluoromethyl)benzoyl]-3,4-dihydro-2H-1,4-benzoxazine + N-methylindan-2-amine hydrochloride (10408-85-2) → (+/-)-3-[2-[(2,3-Dihydro-1H-inden-2-yl)methylamino]ethyl]-6-methoxy-4-[3-(trifluoromethyl)benzoyl]-3,4-dihydro-2H-1,4-benzoxazine ethanedioate

Conditions	Yield
With potassium iodide; oxalic acid; potassium carbonate In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide

N-methylindan-2-amine hydrochloride (10408-85-2) → N2-[5-chloro-2-(4-chlorophenoxy)phenyl]-N2-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N1-(2-piperidin-1-ylethyl)glycinamide (1286264-21-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → N2-[5-chloro-2-(4-chlorophenoxy)phenyl]-N2-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N1-[2-(dimethylamino)ethyl]glycinamide (1286264-19-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C35H42Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C36H44Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C36H42Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C34H38Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C36H42Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C36H42Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → C37H44Cl2N4O5

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → N2-[5-chloro-2-(4-chlorophenoxy)phenyl]-N2-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N1-(2-pyrrolidin-1-ylethyl)glycinamide (1286264-03-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → N2-[5-chloro-2-(4-chlorophenoxy)phenyl]-N2-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N1-methyl(2-pyrrolidin-1-ylethyl)glycinamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

N-methylindan-2-amine hydrochloride (10408-85-2) → N2-[5-chloro-2-(4-chlorophenoxy)phenyl]-N2-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N1-(3-pyrrolidin-1-ylpropyl)glycinamide (1286264-27-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 1 h / 0 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

C16H11Cl2NO4 + N-methylindan-2-amine hydrochloride (10408-85-2) → N-[5-chloro-2-(4-chlorophenoxy)phenyl]-N-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}glycine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 1h;

Upstream product

• 2975-41-9 2,3-dihydro-1H-inden-2-amine 

Downstream Products

• 1286264-27-4 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-(3-pyrrolidin-1-ylpropyl)glycinamide 
• 1286264-03-6 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-(2-pyrrolidin-1-ylethyl)glycinamide 
• 1286264-33-2 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-(piperidin-2-ylmethyl)glycinamide hydrochloride 
• 1286264-15-0 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-[(2S)-pyrrolidin-2-ylmethyl]glycinamide hydrochloride 
• 1286264-12-7 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-(pyrrolidin-3-yl)glycinamide hydrochloride 
• 1286264-08-1 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-(piperidin-3-yl)glycinamide hydrochloride 
• 1286264-00-3 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-[2-(isopropylamino)ethyl]glycinamide hydrochloride 
• 1286263-98-6 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-[2-(ethylamino)ethyl]glycinamide hydrochloride 
• 1286263-94-2 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-[2-(methylamino)ethyl]glycinamide hydrochloride 
• 1286264-19-4 N²-[5-chloro-2-(4-chlorophenoxy)phenyl]-N²-{2-[2,3-dihydro-1H-inden-2-yl(methyl)amino]-2-oxoethyl}-N¹-[2-(dimethylamino)ethyl]glycinamide 

Relevant academic research and scientific papers

Discovery and structural analyses of S-adenosyl-l-homocysteine hydrolase inhibitors based on non-adenosine analogs

Optimization of a new series of S-adenosyl-l-homocysteine hydrolase (AdoHcyase) inhibitors based on non-adenosine analogs led to very potent compounds 14n, 18a, and 18b with IC50 values of 13 ± 3, 5.0 ± 2.0, and 8.5 ± 3.1 nM, respectively. An X-ray crystal structure of AdoHcyase with NAD+ and 18a showed a novel open form co-crystal structure. 18a in the co-crystals formed intramolecular eight membered ring hydrogen bond formations. A single crystal X-ray structure of 14n also showed an intramolecular eight-membered ring hydrogen bond interaction.

THERAPEUTIC AGENT FOR CEREBRAL INFARCTION

The invention provides a therapeutic drug for ischemic stroke. The therapeutic drug has the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof, as an active ingredient.