878671-94-4

Basic information

• Product Name: 1-Naphthalenamine, 4-cyclopropyl-
• Synonyms: 1-Naphthalenamine, 4-cyclopropyl-;4-Cyclopropyl-1-Naphthalenamine;4-Cyclopropylnaphthalen-1-aMine;4-Cyclopropyl-1-naphthalenaMine oxalate;1-phthalemine, 4-cyclopropyl-;1-amino-4-cyclopropylnaphthalene
• CAS NO: 878671-94-4
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.25
• EINECS: 200-001-8
• Product Categories: Lesinurad (RDEA-594)
• Mol File: 878671-94-4.mol

Chemical Properties

• Boiling Point: 361.6°C at 760 mmHg
• Flash Point: 190.3°C
• Appearance: /
• Density: 1.191
• Vapor Pressure: 2.04E-05mmHg at 25°C
• Refractive Index: 1.713
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.62±0.10(Predicted)
• CAS DataBase Reference: 1-Naphthalenamine, 4-cyclopropyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenamine, 4-cyclopropyl-(878671-94-4)
• EPA Substance Registry System: 1-Naphthalenamine, 4-cyclopropyl-(878671-94-4)

Safety Data

• Hazardous Substances Data: 878671-94-4(Hazardous Substances Data)

Usage

Uses

1-Naphthalenamine, 4-cyclopropylis used in Advanced Organic Chemistry:
It serves as a key intermediate in the synthesis of various organic compounds, contributing to the development of new materials and pharmaceuticals.
1-Naphthalenamine, 4-cyclopropylis used in Research Applications:
Due to its unique structure and properties, it is utilized in various research areas to explore its potential applications and understand its interactions with other molecules.
1-Naphthalenamine, 4-cyclopropylis used in Pharmaceutical Development:
Its specific chemical properties make it a promising candidate for the development of new drugs and therapeutic agents.
1-Naphthalenamine, 4-cyclopropylis used in Material Science:
It may be employed in the creation of novel materials with unique properties, such as improved conductivity or enhanced stability.
1-Naphthalenamine, 4-cyclopropylis used in Chemical Synthesis:
It acts as a building block in the synthesis of complex organic molecules, facilitating the development of new chemical compounds with potential applications in various industries.

InChI:InChI=1/C13H13N/c14-13-8-7-10(9-5-6-9)11-3-1-2-4-12(11)13/h1-4,7-9H,5-6,14H2

Synthetic route

1-cyclopropyl-4-nitronaphthalene (878671-93-3) → 1-amino-4-cyclopropylnaphthalene (878671-94-4)

Conditions	Yield
Stage #1: 1-cyclopropyl-4-nitronaphthalene With iron hydroxide oxide In water at 80℃; for 0.5h; Stage #2: With hydrazine In water for 2h; Solvent; Temperature; Reagent/catalyst; Time;	96%
With ammonium chloride; zinc In tetrahydrofuran; water for 10h; Reflux;	89.1%
With ammonium chloride; zinc In tetrahydrofuran; water Reagent/catalyst; Reflux;	87%

4-Bromo-1-naphthylamine (2298-07-9) + cyclopropylboronic acid (411235-57-9) → 1-amino-4-cyclopropylnaphthalene (878671-94-4)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 6h; Suzuki Coupling; Inert atmosphere;	95.3%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 6h; Inert atmosphere;	95.3%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 12h; Inert atmosphere;	83.6%

1-bromo-4-cyclopropylnaphthalene (127971-24-8) → 1-amino-4-cyclopropylnaphthalene (878671-94-4)

Conditions	Yield
With copper(I) oxide; ammonium hydroxide In N,N-dimethyl-formamide at 100℃; for 28h; Solvent; Reagent/catalyst; Temperature; Autoclave; Green chemistry;	80%

1-cyclopropyl-naphthalene (25033-19-6) → 1-amino-4-cyclopropylnaphthalene (878671-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite / 2.5 h / 0 °C 2: hydrogen / palladium 10% on activated carbon / ethanol View Scheme
Multi-step reaction with 2 steps 1: nitric acid / 0 - 20 °C 2: palladium on activated charcoal; hydrogen View Scheme
Multi-step reaction with 2 steps 1: nitric acid / water; dichloromethane 2: palladium on activated charcoal; hydrogen; oxalic acid / ethanol View Scheme
Multi-step reaction with 2 steps 1: nitric acid 2: iron perchlorate hexahydrate; hydrazine hydrate / ethanol / Reflux View Scheme
Multi-step reaction with 2 steps 1: acetic acid; nitric acid / 7 h / 20 °C / Cooling with ice 2: zinc; ammonium chloride / tetrahydrofuran; water / 10 h / Reflux View Scheme

1-Bromonaphthalene (90-11-9) → 1-amino-4-cyclopropylnaphthalene (878671-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 20 °C 2: sodium nitrite / 2.5 h / 0 °C 3: hydrogen / palladium 10% on activated carbon / ethanol View Scheme
Multi-step reaction with 3 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 5 °C 2: nitric acid / 0 - 20 °C 3: palladium on activated charcoal; hydrogen View Scheme
Multi-step reaction with 3 steps 1.1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / Cooling with ice 1.2: 44 h / 20 °C / Reflux; Inert atmosphere 2.1: acetic acid; nitric acid / 7 h / 20 °C / Cooling with ice 3.1: zinc; ammonium chloride / tetrahydrofuran; water / 10 h / Reflux View Scheme

1-amino-naphthalene (134-32-7) + cyclopropylboronic acid (411235-57-9) → 1-amino-4-cyclopropylnaphthalene (878671-94-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); phosphoric acid In water; toluene at 100℃; for 12h; Inert atmosphere;

1-amino-4-cyclopropylnaphthalene (878671-94-4) + phenyl chloroformate (1885-14-9) → C20H17NO2

Conditions	Yield
With potassium carbonate In tetrahydrofuran at -10℃; for 1h; Temperature; Inert atmosphere;	98.5%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → (1-cyclopropylnaphthalen-4-yl)isothiocyanate (878671-95-5)

Conditions	Yield
In dichloromethane at 20℃; for 12h;	96.2%
In dichloromethane at 20℃; for 1h;	80%
In dichloromethane at 20℃;

1-amino-4-cyclopropylnaphthalene (878671-94-4) + 2-nitro-3-(trifluoromethylsulfonyloxy)pyridine (146336-72-3) → N-(4-cyclopropylnaphthalen-1-yl)-2-nitropyridin-3-amine

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 90℃; for 36h; Inert atmosphere;	95.3%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In toluene at 90℃; for 36h; Inert atmosphere;	33.3%

carbon disulfide (75-15-0) + 1-amino-4-cyclopropylnaphthalene (878671-94-4) → (1-cyclopropylnaphthalen-4-yl)isothiocyanate (878671-95-5)

Conditions	Yield
Stage #1: carbon disulfide; 1-amino-4-cyclopropylnaphthalene With potassium carbonate In water; N,N-dimethyl-formamide at 15℃; for 3.5h; Stage #2: With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water; N,N-dimethyl-formamide at 0℃; for 1h; Stage #3: With water; sodium hydroxide In dichloromethane; N,N-dimethyl-formamide for 2h;	94%
Stage #1: 1-amino-4-cyclopropylnaphthalene With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; Stage #2: carbon disulfide In toluene at 20℃; for 7.5h; Stage #3: With p-toluenesulfonyl chloride In toluene at 0℃; for 3h; Reflux;	86.3%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + thiophosgene (463-71-8) → (1-cyclopropylnaphthalen-4-yl)isothiocyanate (878671-95-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h;	86%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h;	86%
Stage #1: 1-amino-4-cyclopropylnaphthalene; thiophosgene With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h; Stage #2: With hydrogenchloride In dichloromethane; water	86%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + C8H15N3O → 3-(3-buten-1-yl)-4-(4-cyclopropylnaphth-1-yl)-4H-1,2,4-triazole

Conditions	Yield
With acetic acid In acetonitrile at 120℃; Inert atmosphere;	81%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + 4-Pentenoic acid hydrazide (86538-23-0) → 3-(3-buten-1-yl)-4-(4-cyclopropylnaphth-1-yl)-4H-1,2,4-triazole

Conditions	Yield
Stage #1: 4-Pentenoic acid hydrazide With N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 50℃; for 2h; Stage #2: 1-amino-4-cyclopropylnaphthalene With acetic acid for 12h; Reflux;	78%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + diazodimedone (1807-68-7) → 4-cyclopropyl-9,9-dimethyl-9,10-dihydro-7H-benzo[kl]acridin-11(8H)-one

Conditions	Yield
With {Ir(η5-C5Me5)(CH3CN)3}{SbF6}2; acetic acid In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;	78%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + diformylhydrazine (628-36-4) → 4-(4-cyclopropylnaphthalene)-1,2,4-triazole

Conditions	Yield
With pyridine; chloro-trimethyl-silane In toluene at 20℃; for 2h; Solvent; Reagent/catalyst; Temperature; Reflux;	78%
With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Reflux;	70%

1-amino-4-cyclopropylnaphthalene (878671-94-4) → C13H12ClN

Conditions	Yield
With N-chloro-succinimide; acetic acid at 20℃; for 16h;	64.47%
With N-chloro-succinimide; acetic acid at 20℃; for 16h;	64.47%

1-amino-4-cyclopropylnaphthalene (878671-94-4) + 3-chloro-2-nitropyridine (54231-32-2) → N-(4-cyclopropylnaphthalen-1-yl)-2-nitropyridin-3-amine

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 90℃; for 12.25h; Inert atmosphere;	60.6%
With palladium acetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere;	60.6%

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (878671-96-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C 2.2: 60 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: dichloromethane / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 50 h View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 2-((5-amino-4-(4-cyclopropyl-naphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid methyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C 2.2: 60 h / 50 °C 3.1: potassium carbonate / 24.08 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide 3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating 4: N,N-dimethyl-formamide / 14 - 22 °C View Scheme
Multi-step reaction with 5 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide 4: sodium hydroxide / N,N-dimethyl-formamide; water / Heating 5: N,N-dimethyl-formamide / 14 - 22 °C View Scheme
Multi-step reaction with 3 steps 1: dichloromethane / 12 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 50 °C 3: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: dichloromethane / 20 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 50 h 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid

Conditions	Yield
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C 2.2: 60 h / 50 °C 3.1: potassium carbonate / 24.08 h / 20 °C 4.1: sodium nitrite; N-benzyl-N,N,N-triethylammonium chloride; Bromoform; dichloro-acetic acid / 3 h / 20 °C 5.1: water; lithium hydroxide / ethanol; tetrahydrofuran / 0.83 h / 0 °C 5.2: 0 °C / pH 7 View Scheme
Multi-step reaction with 6 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 4: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 5: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale 6: sodium hydroxide; water / toluene / 18 - 25 °C View Scheme
Multi-step reaction with 6 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide 3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating 4: N,N-dimethyl-formamide / 14 - 22 °C 5: copper(ll) bromide; potassium nitrite / acetonitrile / 14 - 20 °C 6: sodium hydroxide; water / toluene / 18 - 25 °C View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid methyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C 2.2: 60 h / 50 °C 3.1: potassium carbonate / 24.08 h / 20 °C 4.1: sodium nitrite; N-benzyl-N,N,N-triethylammonium chloride; Bromoform; dichloro-acetic acid / 3 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 4: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 5: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale View Scheme
Multi-step reaction with 5 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide 3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating 4: N,N-dimethyl-formamide / 14 - 22 °C 5: copper(ll) bromide; potassium nitrite / acetonitrile / 14 - 20 °C View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid sodium salt (1151516-14-1)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 50 °C 2.2: 60 h / 50 °C 3.1: potassium carbonate / 24.08 h / 20 °C 4.1: sodium nitrite; N-benzyl-N,N,N-triethylammonium chloride; Bromoform; dichloro-acetic acid / 3 h / 20 °C 5.1: water; lithium hydroxide / ethanol; tetrahydrofuran / 0.83 h / 0 °C 5.2: 0 °C / pH 7 6.1: sodium hydroxide / ethanol; water / 0.25 h / 10 °C View Scheme
Multi-step reaction with 6 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 4: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 5: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale 6: sodium hydroxide / toluene; water / 18 - 25 °C / Large scale View Scheme
Multi-step reaction with 6 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide 3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating 4: N,N-dimethyl-formamide / 14 - 22 °C 5: copper(ll) bromide; potassium nitrite / acetonitrile / 14 - 20 °C 6: sodium hydroxide / toluene; water / 18 - 25 °C / Large scale View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → Reaxys ID: 26486083

Conditions	Yield
Multi-step reaction with 5 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 4: N,N-dimethyl-formamide 5: N-Bromosuccinimide / tetrahydrofuran View Scheme
Multi-step reaction with 6 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide / 50 - 55 °C 4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 5: N,N-dimethyl-formamide 6: N-Bromosuccinimide / tetrahydrofuran View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 3-amino-4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione (878671-96-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide 3: sodium hydroxide / N,N-dimethyl-formamide; water / Heating View Scheme
Multi-step reaction with 4 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide 4: sodium hydroxide / N,N-dimethyl-formamide; water / Heating View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → Reaxys ID: 26486087

Conditions	Yield
Multi-step reaction with 4 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 4: N,N-dimethyl-formamide View Scheme
Multi-step reaction with 5 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide / 50 - 55 °C 4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C 5: N,N-dimethyl-formamide View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → (1-cyclopropylnaphthalen-4-yl)isothiocyanate (878671-95-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene; water 2: potassium hydroxide View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → C15H17N5S*ClH (1533519-90-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide View Scheme
Multi-step reaction with 3 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide View Scheme

1-amino-4-cyclopropylnaphthalene (878671-94-4) → N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide (1533519-86-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C View Scheme
Multi-step reaction with 3 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide / 50 - 55 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / water; N,N-dimethyl-formamide / 3.5 h / 15 °C 1.2: 1 h / 0 °C 1.3: 2 h 2.1: ethyl acetate / 2 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: ethyl acetate 2: ethanol View Scheme

Upstream product

• 2298-07-9 4-Bromo-1-naphthylamine 
• 411235-57-9 cyclopropylboronic acid 
• 878671-93-3 1-cyclopropyl-4-nitronaphthalene 
• 25033-19-6 1-cyclopropyl-naphthalene 
• 127971-24-8 1-bromo-4-cyclopropylnaphthalene 
• 134-32-7 1-amino-naphthalene 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 878671-98-8 2-((5-amino-4-(4-cyclopropyl-naphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid methyl ester 
• 878672-00-5 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid 
• 1533519-86-6 N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide 
• 1533519-84-4 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol 
• 1533519-85-5 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-yl)thio)acetic acid methyl ester 
• 878672-00-5 (-)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid 
• 878672-00-5 (+)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid 

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The invention relates to an imidazopyridine mercaptoacetic acid derivative as well as a preparation method and application thereof. The compound has a structure shown as a formula I or a formula II which is described in the specification. The invention also relates to a preparation method and a pharmaceutical composition of the compound containing the structure shown in the formula I or II. The invention also provides application of the compound in preparation of anti-gout drugs.

Novel Human Urate Transporter 1 Inhibitors as Hypouricemic Drug Candidates with Favorable Druggability

Lesinurad, a human urate transporter 1 (URAT1) inhibitor approved as a medication for the treatment of hyperuricemia associated with gout in 2015, can cause liver and renal toxicity. Here, we modified all three structural components of lesinurad by applying scaffold hopping, bioisosterism, and substituent-decorating strategies. In a mouse model of acute hyperuricemia, 21 of the synthesized compounds showed increased serum uric acid (SUA)-reducing activity; SUA was about 4-fold lower in animals treated with 44, 54, and 83 compared with lesinurad or benzbromarone. In the URAT1 inhibition assay, 44 was over 8-fold more potent than lesinurad (IC50: 1.57 μM vs 13.21 μM). Notably, 83 also displayed potent inhibitory activity (IC50 = 31.73 μM) against GLUT9. Furthermore, we also preliminarily explored the effect of chirality on the potency of the promising derivatives 44 and 54. Compounds 44, 54, and 83 showed favorable drug-like pharmacokinetics and appear to be promising candidates for the treatment of hyperuricemia and gout.

Preparation method of naphthylamine drug intermediate

The invention discloses a preparation method of a naphthylamine drug intermediate. The preparation method of the naphthylamine drug intermediate comprises the steps of: in a solvent, and under the action of the catalyst FeO(OH), carrying out the following reduction reaction on a compound I and hydrazine hydrate to obtain a compound II. The method has the advantages of high purity and yield of product, simple and safe process, and easy operation, and is suitable for large-scale industrial production.

Lesinurad analogue and its preparation method and medical use

The invention relates to a lesinurad analog as shown in the general formula (I), its preparation method, a pharmaceutical composition containing the derivative and an application of the pharmaceutical composition used as a therapeutic agent, especially as a medicine for treating hyperuricemia and gout, wherein definition of each substituent group in the general formula (I) is as the same as definition in the specification.

Preparation method of 4-cyclopropyl-1-naphthylamine

The invention relates to a novel preparation method of 4-cyclopropyl-1-naphthylamine. The raw materials needed for the preparation method are cheap in price and easy to obtain, the reaction step operation is simple, and the total yield is better than that of the prior art level. Moreover, the nitrification, hydrogenation reduction, Suzuki coupling and other reactions are avoided to use, and thus the production difficulty and production cost is greatly reduced. A relatively economical, efficient, safe and environment-friendly synthetic route is provided for the preparation of 4-cyclopropyl-1-naphthylamine.

2-(5-bromo-4-(4-cyclopropyl naphthalen-1-yl)-4H-1,2,4-triazol-3-yl thio)acetic acid intermediates

Lesinurad key intermediate compounds (L-4) and (L-5) are prepared; a preparation method is simple in postprocessing of reaction, the product is relatively high in purity and relatively good in stability, the preparation method is suitable for industrialized production, and a new simple and feasible method is provided for preparation of 2-(5-bromo-4-(4-cyclopropyl naphthalen-1-yl)-4H-1,2,4-triazol-3-yl thio)acetic acid key intermediate compound (L-6) and a final finished product raw material medicine thereof; the pollution to the environment is reduced, the product yield and quality of the prepared raw material medicine are improved to a great extent, and medicine industrialization costs are reduced.

Imidazole [4, 5 - b] pyridine qiu acetyl amine derivative and its preparation method and application

The invention relates to an imidazole [4,5-b] pyridine mercaptoacetamide derivative represented in a formula I and pharmaceutically acceptable salt, ester or prodrug of the derivative, a preparation method of the derivative and an application of composition containing one or more of the compound to preparation of a drug for treating and preventing HIV (human immunodeficiency virus) infection and anti-leukemia or anti-tumor drugs.