864680-71-7

Basic information

• Product Name: 3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl
• Synonyms: 3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl;3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one;3-(4-AMinophenyl)-1,2,4-oxadiazol-5(4H)-one hydrochloride;3-(4-aminophenyl)-1,2,4-Oxadiazol-5(2H)-one;1,2,4-Oxadiazol-5(2H)-one,3-(4-aminophenyl)-
• CAS NO: 864680-71-7
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 213.62102
• Mol File: 864680-71-7.mol

Chemical Properties

• Boiling Point: 314.543 °C at 760 mmHg
• Flash Point: 144.031 °C
• Appearance: /
• Density: 1.55 g/cm³
• PKA: 7.44±0.20(Predicted)
• CAS DataBase Reference: 3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl(864680-71-7)
• EPA Substance Registry System: 3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl(864680-71-7)

Safety Data

• Hazardous Substances Data: 864680-71-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl is used as a potential drug candidate for its anti-inflammatory, analgesic, and antipyretic properties, making it suitable for the development of medications to treat various inflammatory and pain-related conditions.
Used in Neurodegenerative Disease Treatment:
3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl is being researched for its potential use in the treatment of neurodegenerative diseases, such as Alzheimer's and Parkinson's, due to its neuroprotective effects and ability to modulate relevant signaling pathways.
Used as an Anticonvulsant:
3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl is being studied for its potential as an anticonvulsant, which could be used in the development of medications to treat epilepsy and other seizure disorders.
Used in Antimicrobial Applications:
3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl is being investigated for its antimicrobial activities, which could lead to the development of new antibiotics or antifungal agents to combat drug-resistant infections.
Used in Antitumor Applications:
3-(4-aMinophenyl)-1,2,4-oxadiazol-5(4H)-one-HCl is also being studied for its antitumor activities, with potential applications in the development of anticancer drugs that target various types of cancer cells and inhibit tumor growth and progression.

Upstream product

• 105-58-8 Diethyl carbonate 
• 19932-97-9 3-p-nitrophenyl-4,5-dihydro-1,2,4-oxadiazol-5-one 
• 277319-62-7 4-amino-N'-hydroxybenzimidamide 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 872728-83-1 2-[4-(5-oxo-1,2,4-oxadiazol-3-yl)phenylamino]acetic acid ethyl ester 
• 1418267-54-5 2-oxo-2-( 4-(5-oxo-4,5-dihydro-1 ,2,4-oxadiazol-3-yl)phenylamino )-1-( 4'(trifluoromethoxy)biphenyl-3-yl)ethyl acetate 
• 1094107-30-8 C₂₂H₂₄N₄O₅ 
• 1228774-52-4 C₂₁H₂₀N₄O₈S 
• 1228774-48-8 C₂₆H₂₇N₅O₉S 
• 1228774-44-4 C₂₆H₂₅F₂N₅O₇ 
• 1228774-19-3 C₂₆H₂₂F₃N₅O₈ 
• 1228774-13-7 C₂₇H₂₇N₅O₈ 
• 1228772-78-8 [(2R,3R)-3-acetyloxy-4-[N-(2-chloroethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]anilino]-1,4-dioxo-1-[4-(5-oxo-4H-1,2,4-oxadiazol-3-yl)anilino]butan-2-yl]acetate 

Relevant articles and documents

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The invention relates to a process for preparing an optionally substituted 4-benzimidazol- 2-ylmethylamino)-benzamidine, characterised in that (a) an optionally correspondingly substituted diaminobenzene is condensed with 2 [4- (1,2,4-oxadiazol-5-on-3-yl)-phenylamino]-acetic acid, (b) i) the product thus obtained is hydrogenated and ii) optionally the amidino group is carbonylated, without isolating the intermediate product of the hydrogenation beforehand; as well as a process for preparing a salt of an optionally substituted 4(benzimidazol-2-ylmethylamino)-benzamidine, wherein (a) an optionally correspondingly substituted diaminobenzene is condensed with 2-[4-(1,2,4-oxadiazol-5-on-3-yl)-phenylamino]-acetic acid, (b) the product thus obtained is hydrogenated, and (c) i) optionally the amidino group is carbonylated and ii) without prior isolation of the intermediate product of the carbonylation the desired salt is isolated.

IMPROVED PROCESS FOR THE PREPARATION OF THE SALTS OF 4-(BENZIMIDAZOLYLMETHYLAMINO)-BENZAMIDES

The invention relates to a process for preparing a salt of an optionally substituted 4-benzimidazol-2-ylmethylamino)-benzamidine, characterised in that (a) an optionally correspondingly substituted diaminobenzene is condensed with 2-[4-(1,2,4-oxadiazol-5-on-3-yl)-phenylamino]-acetic acid, b) i) the product thus obtained is hydrogenated, ii) optionally the amidino group is carbonylated, without isolating the intermediate product of the hydrogenation beforehand and iii) without prior isolation of the intermediate product of the carbonylation the desired salt is isolated.

Process for the preparation of 4-(benzimidazolylmethylamino)-benzamidines

Production of optionally substituted 4-(benzimidazol-2-ylmethylamino)-benzamidines (I) involves: (a) condensing an optionally substituted diaminobenzene (II) with 2-(4-(1,2,4-oxadiazol-5-on-3-yl)-phenylamino)-acetic acid (III); (b) hydrogenating the product (IV); and (c) optionally carbonylating the amidino group. The intermediates (III), 2-(4-(1,2,4-oxadiazol-5-on-3-yl)-aniline (V) and benzimidazole derivatives (IV') are new compounds. Independent claims are included for the following new intermediates: 2-(4-(1,2,4-oxadiazol-5-on-3-yl)-phenylamino)-acetic acid of formula (III), 2-(4-(1,2,4-oxadiazol-5-on-3-yl)-phenylaminomethyl)-benzimidazoles of formula (IV') and 2-(4-(1,2,4-oxadiazol-5-on-3-yl)-aniline of formula (V). R 1> : alkyl or cycloalkyl; R 2> : alkyl (optionally substituted (os) by cycloalkyl-(1-3C) alkyl, where the 1-3C alkyl is os by COOH or a group convertible in vivo to COOH); or NR 21>R 22>; R 21> : alkyl (os by COOH, alkoxycarbonyl, COOCH 2Ph, CONHSO 2T, CONHSO 2Ph, 'trifluorosulfonylamino' (sic), trifluorosulfonylaminocarbonyl' (sic), or 1H-tetrazolyl); 2-4C alkyl substituted (but not on the alpha -C adjacent to the N) by OH, -O-T-Ph, -NH-T-COOH, -NH-T-COOT, -N(T)-T-COOH or -N(T)-T-COOT; or piperidinyl (os by T); R 22> : H; alkyl; cycloalkyl (os by T); 3-6C alkenyl or 3-6C alkynyl (both with the unsaturated part not bonded directly to N); phenyl (os by F, Cl, Br, T or OT); or benzyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrrolyl, thienyl or imidazolyl (all os by T); or NR 21>R 22> : 5-7 membered cycloalkyleneimino (os by COOH or (1-4C) alkoxycarbonyl and optionally fused with a benzene ring); T : 1-3C alkyl; alkyl groups have 1-6C and cycloalkyl groups 3-7C unless specified otherwise. [Image] ACTIVITY : Anticoagulant. MECHANISM OF ACTION : Thrombin inhibitor.