81403-67-0

Basic information

• Product Name: Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide
• Synonyms: Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide;2-Furancarboxamide,tetrahydro-N-[3-(methylamino)propyl]-;N-(3-(MethylaMino)propyl)tetrahydrofuran-2-carboxaMide;N-[3-(METHYLAMINO)PROPYL]-2-TETRAHYDROFURAN-CARBOXAMIDE(AF4)
• CAS NO: 81403-67-0
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25142
• EINECS: 1806241-263-5
• Product Categories: Drug Intermediates
• Mol File: 81403-67-0.mol

Chemical Properties

• Boiling Point: 380.81 °C at 760 mmHg
• Flash Point: 184.108 °C
• Appearance: /
• Density: 1.045 g/cm³
• PKA: 14.93±0.20(Predicted)
• CAS DataBase Reference: Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide(81403-67-0)
• EPA Substance Registry System: Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide(81403-67-0)

Safety Data

• Hazardous Substances Data: 81403-67-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide serves as a key intermediate in the synthesis of potential drug candidates, particularly for the development of new therapeutic agents. Its unique structure allows it to interact with biological targets, making it a promising candidate for the treatment of certain medical conditions.
Used in Chemical Manufacturing:
In the chemical manufacturing industry, Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide may be utilized as a building block or a component in the production of other complex organic compounds, contributing to the synthesis of a wide range of chemical products.
Used in Material Science:
Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide's structural features and chemical properties may also find applications in material science, where it could be used to develop new materials with specific properties, such as improved stability, reactivity, or biocompatibility.
While the specific applications and industries may vary, the versatility of Tetrahydrofuran-2-CarboxylicAcid(3-Methylamino-Propyl)-Amide is evident in its potential use across different sectors, highlighting its importance in scientific research and industrial applications.

Upstream product

• 72104-44-0 tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide 
• 16874-33-2 tetrahydro-2-furancarboxylic acid 
• 6291-84-5 N-Methyl-1,3-propanediamine 
• 52449-98-6 tetrahydrofuran-2-carbonyl chloride 
• 167391-50-6 C₈H₁₂O₅ 
• 37443-42-8 methyl tetrahydrofuran-2-carboxylate 

Downstream Products

• 81403-80-7 alfuzosin 
• 81403-68-1 alfuzosin hydrochloride 

Relevant articles and documents

Improved method used for preparing quinazoline drugs

The invention relates to an improved method used for preparing quinazoline drugs, and provides a synthesis route taking 2-chloro-4-amino-6,7-dimethoxyquinazoline as an intermediate. The synthesis route comprises following steps: acrylonitrile and a methylamine alcohol solution are subjected to amination reaction so as to obtain intermediate (I); triethylamine is taken as an acid binding agent, andbenzyl chloride is taken as a protective group so as to obtain an intermediate (II); a metal hydride is adopted so as to obtain an intermediate (III) through reduction; acylation with tetrahydro-2-furancarbonylchloride is carried out so as to obtain an intermediate (IV); the intermediate (IV) and ammonium formate are subjected to hydrogenolysis under catalytic effect of palladium on carbon so asto obtain an intermediate (V); and at least condensation reaction with 2-chloro-4-amino-6,7-dimethoxyquinazoline is carried out so as to obtain quinazoline drug Alfuzosin Hydrochloride (VI). Comparedwith the prior art, the improved method possesses following advantages: operation is simple and safe; reaction conditions are convenient to control; energy consumption is low; yield is stable; and industrialized application prospect is promising.

A process for the preparation of alfuzosin hydrochloride method (by machine translation)

The invention relates to a process for the preparation of alfuzosin hydrochloride method, method comprises the following steps: (1) 15 °C following, acrylonitrile into the the methylamine is mellow solution to stir, by distillation to obtain (I); (2) to (I) is dripped reducing agent in an organic solvent, heating to reflux, then slowly sequentially into the 25% sodium hydroxide solution and distilled water, by the distillation treatment to obtain the (II); (3) under dry condition, the thionyl chloride is slowly dripped into the 2 - tetrahydrofuran formic acid, a 2 - tetrahydrofuran chloride; (4) the temperature control in the 5 - 15 °C conditions, will be 2 - tetrahydrofuran formyl the chlorine drips into containing acid, organic solvent and (II) of the mixed solution, then completing the stirring 3 hours, for 25% sodium hydroxide solution to neutralize, by organic solvent extraction, (III) be; (5) to (III) with 2 - chloro - 4 - amino - 6, 7 - dimethoxy quinazoline in presence of organic solvent, reflux stirring 4 - 10 hours, cooling and filtering, and steaming and removing the organic solvent, acetone dispersed precipitate solid, then re-crystallizing mixed solvent, to get the alfuzosin hydrochloride (IV). (by machine translation)

Chemoselective calcium-catalysed direct amidation of carboxylic esters

Unactivated carboxylic esters and primary amines undergo calcium-catalysed direct amide bond formation in excellent yields under homogeneous conditions in toluene. This green and mild reaction proceeds chemoselectively with esters, whereas related carboxylic acids and amides remain unreactive.

PREPARATION OF ALFUZOSIN

A process for preparing alfuzosin or a salt thereof, which minimizes the concentration of an N1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-N1-methyl-N 2-(4-amino-6,7-dimethoxyquinazolin-2-yl)-propane-1,3-diamine impurity in the product.

AN IMPROVED AND INDUSTRIAL PROCESS FOR THE PREPARATION OF ALFUZOSIN HYDROCHLORIDE AND ITS NOVEL POLYMORPHS

An improved and industrial process for the preparation of Alfuzosin Hydrochloride and its novel polymorphs (Formula (I)).

HMDS-promoted in situ amidation reactions of carboxylic acids and amines

A number of N-acylalkylenediamines were synthesized in high yields by in situ monoamidation of carboxylic acids with diamines. The amidation reactions were carried out simply by heating the substrates at 110 °C for 5-24 h in the presence of HMDS.

Synthesis and antihypertensive activity of a series of 4-amino-6,7-dimethoxyquinazoline derivatives

A series of N2-[(acylamino)alkyl]-6,7-dimethoxy-2,4-quinazolinediamines was synthesized as potential α1-adrenoceptor antagonists. When administered to spontaneously hypertensive rats at 10 mg/kg po, a number of propanediamine derivatives showed good antihypertensive activity, whereas the ethanediamine derivatives, albeit being structurally more closely related to prazosin, were devoid of this property. The most active derivative, N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro- 2-furancarboxamide hydrochloride, alfuzosin, showed high selectivity for peripheral α1-postjunctional adrenoceptors. At equiactive antihypertensive doses, its effect on the pressor response to postural changes in conscious dog was less marked than that shown by prazosin. In the light of these results, alfuzosin was selected for clinical evaluation.