69048-98-2

Basic information

• Product Name: 1-ethyl-1,2-dihydro-5H-tetrazol-5-one
• Synonyms: 5H-Tetrazol-5-one,1-ethyl-1,2-dihydro-;1-ethyl-1,2-dihydro-5H-tetrazol-5-one;1-Ethyltetrazolinone;1-Ethyl-1,4-dihydro-5H-tetrazol-5-one;1-Ethyl-1,4-dihydro-5H-tetrazol-5-one,98+%;1-Ethyl-1H-tetrazol-5(4H)-one;1-ethyl-2H-1,2,3,4-tetrazol-5-one;1-ethyl-2H-tetrazol-5-one
• CAS NO: 69048-98-2
• Molecular Formula: C₃H₆N₄O
• Molecular Weight: 114.10594
• EINECS: 273-844-2
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 69048-98-2.mol

Chemical Properties

• Melting Point: 80℃
• Boiling Point: 121℃
• Flash Point: 27℃
• Appearance: /
• Density: 1.55
• Vapor Pressure: 15.1mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• PKA: -1.42±0.20(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 1-ethyl-1,2-dihydro-5H-tetrazol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethyl-1,2-dihydro-5H-tetrazol-5-one(69048-98-2)
• EPA Substance Registry System: 1-ethyl-1,2-dihydro-5H-tetrazol-5-one(69048-98-2)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 69048-98-2(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE-BROWNISH CRYSTALS OR POWDER

Uses

Intermediate for the synthesis of Alfentanil

InChI:InChI=1/C3H6N4O/c1-2-7-3(8)4-5-6-7/h2H2,1H3,(H,4,6,8)

Upstream product

• 109-90-0 ethyl isocyanate 
• 4648-54-8 trimethylsilylazide 
• 79-03-8 propionyl chloride 
• 1217900-86-1 1-ethyl-5-methylsulfanyl-1H-tetrazole 

Downstream Products

• 69049-03-2 1-(2-chloroethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one 
• 84501-67-7 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl bromide 
• 69049-41-8 N-<1-<2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)-2-phenylethyl>-4-(methoxymethyl)-4-piperidinyl>-N-phenylpropanamide 
• 104072-14-2 1-ethyl-4-{2-[4-methoxymethyl-4-(N-propionyl-anilino)-piperidine-1-yl]-1-methyl-ethyl}-1,4-dihydro-tetrazol-5-one 
• 69221-39-2 N-<1-<2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)propyl>-4-(methoxymethyl)-4-piperidinyl>-N-phenylpropanamide 

Relevant articles and documents

TETRAZOLONE SUBSTITUTED STEROIDS AND USE THEREOF

The present disclosure relates to compounds of formula (AI), (I), (AII), and (II), or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof, a pharmaceutical composition comprising a compound of formula (AI), (I), (AII), and (II), and use thereof, wherein R2, R3, R4, R5, R6, R7, R10, R11a, R11b, R12, R16, R19a, R19b, and R20 are described herein. Such compounds are envisioned useful for the prevention and treatment of a variety of CNS-related conditions, for example, treatment of sleep disorders, mood disorders, movement disorders, convulsive disorders, schizophrenin spectrum disorders, disorders of memory and/or cognition, personality disorders, autism spectrum disorders, pain, traumatic brain injury, vascular diseases, substance abuse disorders and/or withdrawal syndromes, or tinnitus etc.

Preparation method of alfentanil and sufentan and compounds used for preparation of sufentanil and alfentan

The invention discloses a preparation method of alfentanil and sufentan and compounds used for preparation of sufentanil and alfentan. Specifically, the method for preparation of a compound shown as formula V includes: carrying out BOC reaction on a compound shown as formula IV to obtain the compound shown as formula V in the specification. The method can conveniently, efficiently and safely prepare an intermediate product for synthesis of alfentanil and sufentan, i.e. the compound shown as formula V. And then, the compound shown as formula V can be effectively used for preparation of alfentanil and sufentan.

Tetrazolones as a Carboxylic Acid Bioisosteres

The present disclosure provides compounds that include a tetrazolone derivative of a carboxyl group of an active agent. This disclosure also relates to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, and processes for preparing these compounds.

A one-pot synthesis of tetrazolones from acid chlorides: Understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs

A one-pot and scalable synthesis of tetrazolones (tetrazol-5-ones) from acid chlorides using azidotrimethylsilane is presented. The reaction tolerates many functional groups and can furnish aryl-, heteroaryl-, alkenyl-, or alkyl-substituted tetrazolone products in moderate to excellent yield (14-94%). No reduction in yield was observed when the reaction was undertaken on a larger-scale (20-36 g). The method could be used for the late-stage functionalization of pharmaceuticals, to provide tetrazolone congeners of the marketed drugs aspirin, indomethacin, probenecid, telmisartan, bexarotene, niacin (vitamin B3), and the active metabolite of the recently-launched immuno-modulatory agent, BG-12 (Tecfidera). The ability of a tetrazolone group to serve as a bioisostere of a carboxylic acid, and to improve drug pharmacokinetic profiles is also highlighted.

SUBSTITUTED 4-AMINO-PIPERIDINES

The present invention relates to new substituted 4-amino-piperidine opioid receptor modulators, pharmaceutical compositions thereof, and methods of use thereof

Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

Chemotherapy and chemoprophylaxis of influenza is one of the most important directions of health protection activity. Due to the high rate of drug-resistant strains of influenza virus, there is a need for the search and further development of new potent antivirals against influenza with a broad spectrum of activity. In the present study, a set of di-, tri- and tetrazole derivatives of adamantane was efficiently prepared and their anti-influenza activities evaluated against rimantadine-resistant strain A/Puerto Rico/8/34. In general, derivatives of tetrazole possessed the highest virus-inhibiting activity. We demonstrated that several compounds of this set exhibited much higher activity than the currently used antiviral rimantadine, a compound of related structure. Moreover, we showed that these azolo-adamantanes were significantly less toxic. This study demonstrates that influenza viruses can be inhibited by adamantyl-azoles and thus have potential for developing antiviral agents with an alternate mechanism of action.

Process for the preparation of 1-4-disubstituted-5 (4H)-tetrazolinones

1,4-Disubstituted-5(4H)-tetrazolinones of the formula (I) STR1 wherein R1, R2 and R3 have the meanings given in the specification), which are known to be useful as herbicides, can be obtained in very good yields by reacting the corresponding 1-substituted-5(4H)-tetrazolinones with the corresponding carbamoyl chlorides in the presence of 4-dimethylaminopyridine.

Process for the preparation of 1-substituted-5(4H)-tetrazolinones

A process for the preparation of a 1-substituted-5(4H)-tetrazolinone of the formula STR1 wherein R1 is defined in the specification n is 0, 1, 2, 3 or 4, which comprises reacting a 1-substituted-5(4H)-tetrazolinethione of the formula STR2 with an ethylene oxide of the formula STR3 wherein R2 represents hydrogen, methyl or ethyl, in the presence of a base and in the presence of water, an alcohol or a mixture thereof.

(4-piperidinylmethyl and -hetero) purines

(4-Piperidinylmethyl and -hetero)purines having antihistaminic properties and being useful agents in the treatment of allergic diseases.

Synthetic 1,4-Disubstituted-1,4-dihydro-5H-tetrazol-5-one Derivatives of Fentanyl: Alfentanil (R 39209), a Potent, Extremely Short-Acting Narcotic Analgesic

The synthesis of a series of N-1,4-disubstituted-1,4-dihydro-5H-tetrazol-5-one piperidinyl derivatives of fentanyl (10), carfentanil (11), and sufentanil (12) is described.The 1-substituted tetrazolinones 2 were essentially prepared via the addition reaction of aluminum azide to isocyanates or acid chlorides in tetrahydrofuran.Alkylation of 2 under neutral or weakly basic conditions afforded almost exclusively the 1,4-disubstituted tetrazolinone isomer 3.N-Alkylation of the piperidine derivatives 4 with 3 in dimethylformamide yielded 9a-v.The morphinomimetic activity in rats, after intravenous injection of the compounds, was evaluated in the tail withdrawal reflex test.The fentanyl analogues 9a-c (R4 = H) are inactive at the measured dose of 2.5 or 10 mg/kg (iv).For the carfentanil analogues (R4 = COOCH3) maximal narcotic activity is found when R1 represents a lower alkyl group (9d-f) or a thienylethyl group (9n).The sufentanil analogues (R4 = CH2OCH3) show the same structure-activity relationship (SAR) profile as the carfentanil derivatives (R4 = COOCH3).The structural requirements for optimal activity are in good agreement with earlier observations in the series of 10-12.From the series the ethyl tetrazolinone derivative 9r, alfentanil (R 39209), was selected for clinical investigation.As an analgesic in rats, 9r is 140 times more potent then pethidine 15 and 72 times more potent than morphine 14.Alfentanil reaches its peak effect within 1 min after injection, and its duration of action is very short; at 2 times its MED50, 9r has a duration of action of 11 min.This duration is 30 min for 10 and 90 min for 14.Compared to 10, alfentanil 9r is about 4 times faster but 3 times shorter acting.Structurally, 9r shows most resemblance to sufentanil 12, since it differs only by substitution of a 4-ethyltetrazolinone ring for the thiophene ring.The considerable differences in their pharmacological profiles were explained in terms of marked variations in physicochemical and, hence, pharmacokinetic properties.