55863-02-0

Basic information

• Product Name: N-Methyl-1-amino-hex-5-ene
• Synonyms: N-Methyl-1-amino-hex-5-ene;5-HEXEN-1-AMINE, N-METHYL-;N-methylhex-5-en-1-amine;5-Hexen-1-aMine, N-Methyl-N-Methylhex-5-en-1-aMine;N-methyl-5-hexen-1-amine
• CAS NO: 55863-02-0
• Molecular Formula: C₇H₁₅N
• Molecular Weight: 113.202
• Mol File: 55863-02-0.mol

Chemical Properties

• Boiling Point: 146.5±19.0 °C(Predicted)
• Appearance: /
• Density: 0.764±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.74±0.10(Predicted)
• Stability: Volatile
• CAS DataBase Reference: N-Methyl-1-amino-hex-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-1-amino-hex-5-ene(55863-02-0)
• EPA Substance Registry System: N-Methyl-1-amino-hex-5-ene(55863-02-0)

Safety Data

• Hazardous Substances Data: 55863-02-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Methyl-1-amino-hex-5-ene is used as a reagent for the synthesis of various pharmaceutical compounds, particularly those with potential therapeutic applications. Its ability to form new chemical entities makes it a valuable component in the development of novel drugs.
Used in Antiviral Applications:
In the field of antiviral drug development, N-Methyl-1-amino-hex-5-ene is used as a reagent to prepare quinazoline substituted cyclopentane and proline-urea based macrocycles. These compounds have been identified as inhibitors of the Hepatitis C virus (HCV) NS3/4A protease, which plays a crucial role in the viral replication process. By inhibiting this protease, the development and spread of HCV can be effectively controlled, offering a potential treatment option for patients suffering from Hepatitis C.

Upstream product

• 2695-47-8 6-Bromo-1-hexene 
• 74-89-5 methylamine 
• 922520-05-6 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 
• 821-41-0 5-Hexen-1-ol 
• 34825-70-2 hex-5-en-1-amine 
• 593-51-1 methylamine hydrochloride 
• 50347-17-6 N-Methyl-6-hydroxyhexylamine 

Downstream Products

• 671-36-3 1,2-dimethylpiperidine 
• 922726-52-1 4-nitro-benzoic acid (3S,5S)-5-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-(hex-5-enyl-methyl-carbamoyl)-pyrrolidin-3-yl ester 
• 923586-40-7 C₂₈H₃₆N₄O₈ 
• 923274-31-1 (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate 
• 1239316-41-6 C₃₇H₄₃FN₄O₆ 
• 923274-74-2 (1R,2S)-1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-8-methyl-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylic acid ethyl ester 
• 1239316-42-7 C₃₈H₄₅FN₄O₆ 
• 923275-32-5 (1R,2S)-1-{[(1R,2R,4R)-4-[2-(3-fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester 
• 923275-12-1 (1R,2S)-1-({(1R,2R,4R)-2-(hex-5-enyl-methyl-carbamoyl)-4-[7-methoxy-2-(4-methoxy-phenyl)-8-methyl-quinazolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester 
• 922727-92-2 (1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentane carboxylic acid 
• 922727-93-3 (1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester 
• 1042695-88-4 C₃₁H₃₉N₃O₅S 
• 1042695-87-3 methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate 
• 923604-56-2 ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate 

Relevant articles and documents

Toward the Synthesis of Fluorinated Analogues of HCV NS3/4A Serine Protease Inhibitors Using Methyl α-Amino-β-fluoro-β-vinylcyclopropanecarboxylate as Key Intermediate

Synthesis of fluorocyclopropyl building blocks, which constitute the core of various therapeutic agents against the hepatitis C virus, is described. The relevant methyl α-amino-β-fluoro-β-vinylcyclopropanecarboxylate has been used as a key intermediate for the total synthesis of a fluorinated analogue of Simeprevir (TMC 435), a HCV NS3/4A protease inhibitor.

Synthesizing process of N-methyl-5-hexene-1-amine

The invention discloses a synthesizing process of N-methyl-5-hexene-1-amine, and relates to the technical field of medicine synthesis and removes the potential safety hazard that explosive hydrogen isgenerated in the existing process. The synthesizing process comprises the following steps: adding methylamine solution containing methylamine and a solvent into a reaction flask and then adding 6-bromine-1-hexene into the reaction flask, wherein the molar equivalent of methylamine is greater than that of 6-bromine-1-hexene; stirring the mixture; performing oil-bath heating to 40-50 DEG C, performing a reaction for 2-3h, cooling to 20 DEG C, adding a stabilizing agent, then adding sodium hydroxide, recycling excessive methylamine solution under negative pressure, heating to 50-60 DEG C, and performing reduced pressure distillation, so as to obtain colorless liquid, namely, the N-methyl-5-hexene-1-amine. According to the process, the explosive hydrogen is not generated, the synthesizing process is safe, no organic solvent extraction process exists, the process is environmentally friendly, and the product purity is high.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

POLYMORPHIC FORMS OF A MACROCYCLIC INHIBITOR OF HCV

Provided are crystalline forms of the compound of formula (I), which is a macrocyclic inhibitor of HCV, processes for the preparation thereof, and pharmaceutical compositions comprising these crystalline forms.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of Formula (I) and the salts and stereoisomers thereof, wherein each dashed line (represented by - - - - -) represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1 -6alkyl, C3 -7cycloalkyl; n is 3, 4, 5, or 6; R4 is C1-6alkyl or C3-7cycloalkyl; R5 is hydrogen, halo, C1-6alkyl, hydroxy, C1 -6alkoxy, polyhaloC1 -6alkyl; R6 is hydrogen, C1-6alkoxy, mono- or diC1 -6alkylamino; or R5 and R6 may form a 5- or 6-membered unsaturated or partially unsaturated ring, optionally co mprising one or two selected from O, N and S; R7 is hydrogen; C3-7cycloalkyl optionally subst ituted with C1-6alkyl; or C1-6alkyl optionally subst ituted with C3 -7cycloalkyl; R8 is C3-7cycloalkyl optionally subst ituted with C1 -6alkyl; C1 -6alkyl optionally substituted with C3-7cycloalkyl; or -NR8aR8b; R8a and R8b are C1-6alkyl, or both may form a 5- or 6-membered saturated heterocyclic ring; pharmaceut ical compositions containing compounds (I) and processes for preparing compounds (I).

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers thereof, wherein X is N, CH and where X bears a double bond it is C; R1 is -OR5, -NH-SO2R6; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, or C3-7cycloalkyl; R4 is isoquinolinyl optionally substituted with one, two or three substituents each independently selected from C1-6alkyl, C1-6alkoxy, hydroxy, halo, polyhalo- C1-6alkyl, polyhaloC1-6alkoxy, amino, mono- or diC1-6alkylamino, mono- or DiC1-6alkylaminocarbonyl, C1-6alkylcarbonyl-amino, aryl, and Het; n is 3, 4, 5, or 6; each dashed line (represented by ) represents an optional double bond; R5 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R6 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; each aryl is phenyl optionally substituted with one, two or three substituents; and each Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms each independently selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

MACROCYLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I), and the N-oxides, salts, and stereoisomers thereof, wherein each dashed line represents an optional double bond; X is Ν, CH and where X bears a double bond it is C; R1a and R1b are hydrogen, C3-7cycloalkyl, aryl, Het, C1-6alkoxy, C1-6alkyl optionally substituted with halo, C1-6alkoxy, cyano, polyhaloC11-6alkoxy, C3-7cycloalkyl, aryl, or with Het; or R1a and R1b together with the nitrogen to which they are attached form a 4 to 6 membered heterocyclic ring which may be optionally substituted; L is a direct bond, -O- , -O-C1-4alkanediyl-, -O-CO-, -O-C(=O)-ΝR5a - or -O -C(=O)-NR5a-C1-4alkanediyl-; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl, amino, mono- or diC1-6alkylamino; R4 is aryl or a saturated, a partially unsaturated or completely unsaturated 5 or 6 membered monocyclic or 9 to 12 membered bicyclic heterocyclic ring system wherein said ring system contains one nitrogen, and optionally one to three additional heteroatoms selected from O, S and N, and wherein the remaining ring members are carbon atoms; wherein said ring system may be optionally substituted; n is 3, 4, 5, or 6; p is 1 or 2; aryl is phenyl, naphthyl, indanyl, or 1,2,3,4-tetrahydronaphthyl, each of which may be optionally substituted with one, two or three substituents; and Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from N, O and S , being optionally condensed with a benzene ring, and wherein Het may be optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I).

Low background FRET-substrates for lipases and esterases suitable for high-throughput screening under basic (pH 11) conditions

FRET-based fluorogenic substrates for lipases and esterases were prepared in four steps from commercially available building blocks. The substrates are pyrenebutyric acid monoesters of aliphatic 1,2-diols bearing a dinitrophenylamino group as a quencher. The most enzyme-reactive substrate is ester 2a. The substrates do not show any measurable background reaction in the absence of enzyme even at pH 11, but react fast and specifically with lipases and esterases. These substrates offer an unprecedented and practical solution to the long-standing problem of a simple yet efficient high-throughput screening tool for lipase activities under basic conditions. The Royal Society of Chemistry 2006.

Hydroamination/cyclization of aminoalkenes using cationic zirconocene and titanocene catalysts

Alternative catalysts: The hydroamination of nonactivated double bonds has been the domain of rare-earth-metal catalysts. Now alkyl zirconocene and titanocene cations, which are readily prepared from commercially available precursors, are shown to be active catalysts in the hydroamination/cyclization of secondary aminoalkenes to give tertiary pyrrolidines and piperidines.