63486-45-3

Usage

Uses

Used in Organic Synthesis:
1,3-Cyclopentanediamine,cis-(9CI) is used as a building block in organic synthesis for the construction of nitrogen-containing compounds. Its cyclic structure and amine groups provide a versatile platform for the synthesis of a wide range of organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Coordination Chemistry:
In coordination chemistry, 1,3-Cyclopentanediamine,cis-(9CI) serves as a ligand, forming complexes with various metal ions. These complexes exhibit unique properties and applications, such as catalysis, sensing, and materials science.
Used in Polymer Production:
1,3-Cyclopentanediamine,cis-(9CI) is utilized in the production of polymers, where its cyclic structure and amine groups contribute to the formation of polymer chains with specific properties. These polymers can be used in various industries, such as coatings, adhesives, and plastics, depending on their characteristics.
Used in Pharmaceutical Industry:
1,3-Cyclopentanediamine,cis-(9CI) is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form nitrogen-containing compounds makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 1,3-Cyclopentanediamine,cis-(9CI) is employed as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its versatility in organic synthesis allows for the development of new compounds with improved efficacy and selectivity.
Used in Materials Science:
1,3-Cyclopentanediamine,cis-(9CI) is utilized in materials science for the development of novel materials with specific properties. Its coordination chemistry applications enable the creation of metal-organic frameworks and other advanced materials with potential uses in catalysis, gas storage, and sensing.

Synthetic route

C13H16N4O2 → (1R,3S)-cyclopentane-1,3-diamine (63486-45-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 30℃; for 16h;	93%

di-tert-butyl dicarbonate (24424-99-5) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) + 3,6-diiodopyridazine (20698-04-8) → C24H40N6O4

Conditions	Yield
Stage #1: (1R,3S)-cyclopentane-1,3-diamine; 3,6-diiodopyridazine With potassium phosphate; copper(l) iodide; N,N-dimethyl-formamide; ethylene glycol for 12h; Heating; Stage #2: di-tert-butyl dicarbonate In ethylene glycol; ethyl acetate at 25℃; for 1h;	74%

methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (1206102-08-0) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → C20H21N3O3

Conditions	Yield
With acetic acid In toluene at 90℃; for 1.5h;	57%

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) + C15H14F2N6 + 1,1'-carbonyldiimidazole (530-62-1) → 1-((1R,3S)-3-aminocyclopentyl)-3-(6-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)urea

Conditions	Yield
Stage #1: C15H14F2N6; 1,1'-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 1h; Stage #2: (1R,3S)-cyclopentane-1,3-diamine In toluene for 8h;	56.4%

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → N,N'-bis-(3-amino-cyclopentyl)-pyridazine-3,6-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C View Scheme

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → N,N'-bis-[3-(tetrazolo[1,5-b]pyridazin-6-ylamino)-cyclopentyl]-pyridazine-3,6-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C 3.1: 0.094 g / K2CO3 / dimethylformamide / 8 h / 95 °C View Scheme

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → C46H80N12P2

Conditions	Yield
Multi-step reaction with 4 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C 3.1: 0.094 g / K2CO3 / dimethylformamide / 8 h / 95 °C 4.1: 60 percent / acetonitrile / 3 h / Heating View Scheme

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → C60H86N12O8

Conditions	Yield
Multi-step reaction with 5 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C 3.1: 0.094 g / K2CO3 / dimethylformamide / 8 h / 95 °C 4.1: 60 percent / acetonitrile / 3 h / Heating 5.1: toluene / 24 h / Heating View Scheme

4,7-dichloroquinoline (86-98-6) + dimethanesulphonate + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → cis-N,N'-bis-(7-chloroquinolin-4-yl)-cyclopentane-1,3-diamine

Conditions	Yield
With methanesulfonic acid; triethylamine In diethyl ether; acetic acid

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) + C12H8ClN3O → C17H19N5O

Conditions	Yield
With triethylamine In ethanol at 120℃; for 1h;

5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (1448694-38-9) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → (1R,3S)-N-[3-(4-methoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]cyclopentane-1,3-diamine

Conditions	Yield
In 2-methoxy-ethanol at 80℃; for 3h;

5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (1448694-38-9) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → (1S,3R)-N-[3-(4-methoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]cyclopentane-1,3-diamine

Conditions	Yield
In 2-methoxy-ethanol at 80℃; for 3h;

Upstream product

• 1013640-20-4 cyclopentane-1,3-dioxime 
• 3859-41-4 1,3-cyclopentadione 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 98-00-0 (2-furyl)methyl alcohol 

Relevant academic research and scientific papers

Bio-based synthesis of cyclopentane-1,3-diamine and its application in bifunctional monomers for poly-condensation

A novel and green route for the synthesis of cyclopentane-1,3-diamine (CPDA) from hemicellulosic feedstock is established in this work. Through many explorations and optimizations, the single successful multi-step synthesis was found to comprise: (1) the Piancatelli rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone (4-HCP), (2) a highly improved isomerization of4-HCPinto cyclopentane-1,3-dione (CPDO) using the Ru Shvo catalyst, (3) conversion ofCPDOinto cyclopentane-1,3-dioxime (CPDX), and (4) a mild oxime hydrogenation ofCPDXover Rh/C to afford the desiredCPDA. In addition, diastereomerically purecis- andtrans-isomers ofCPDAwere reacted with (A) bio-based lactones, and (B) 5-(hydroxymethyl)furfural (HMF) to synthesize novel bifunctional diol monomers with internal amide and imine groups, respectively. Monomer5, derived using γ-valerolactone (GVL), was successfully applied in the synthesis of polyurethanes.

TETRACYCLIC HETEROCYCLE COMPOUNDS USEFUL AS HIV INTEGRASE INHIBITORS

The present invention relates to Tetracyclic Heterocycle Compounds of Formula (I) and pharmaceutically acceptable salts or prodrug thereof, wherein n, X, Y, Z, R1, R2, and R3 are as defined herein. The present invention also relates to compositions comprising at least one Tetracyclic Heterocycle Compound, and methods of using the Tetracyclic Heterocycle Compounds for treating or preventing HIV infection in a subject.

3-Anilino-2,4-diazabicyclo[3.2.1]octenes

Novel 3-anilino-2,4-diazabicyclo[3.2.1]octenes, physiologically tolerable acid addition salts thereof and method of preparing same are described. These compounds are useful as tranquilizers, diuretics and antihypertensives.