103335-41-7

Basic information

• Product Name: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE
• Synonyms: METHYL 3-OXO-4-AZA-5-ALPHA-ANDROST-1-ENE-17-BETA-CARBOXYLATE;3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-Tetradecahydro-4a,6a-diMethyl-2-oxo-;Finasteride Methyl Ester Analog;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-Methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7, 8,9,9a,9b,10,11,11a-t;(4aR,4bS,6aS,7S,9aS,9bS,11aR);-Methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylate;(4aR,4bS,6aS,7S,9aS,9bS,11aR)-Methyl 4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a
• CAS NO: 103335-41-7
• Molecular Formula: C₂₀H₂₉NO₃
• Molecular Weight: 331.46
• Product Categories: Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 103335-41-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 280-282°C (dec.)
• Boiling Point: 478.615 °C at 760 mmHg
• Flash Point: 243.258 °C
• Appearance: Off-White Solid
• Density: 1.114 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 14.15±0.70(Predicted)
• CAS DataBase Reference: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE(103335-41-7)
• EPA Substance Registry System: METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE(103335-41-7)

Safety Data

• Hazardous Substances Data: 103335-41-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 103335-41-7 differently. You can refer to the following data:
1. Finasteride (F342000) and Dutasteride (D735000) impurity. An intermediate in the synthesis of Finasteride and Dutasteride, 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia ac ne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders.
2. 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester (Finasteride EP Impurity B) is an impurity of Finasteride (F342000) and Dutasteride (D735000). An intermediate in the synthesis of Finasteride and Dutasteride, 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders. Finasteride impurity.
3. Finasteride (F342000) impurity. A novel intermediate in the synthesis of Finasteride, a 5α-reductase inhibitor used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders.

InChI:InChI=1/C20H29NO3/c1-19-10-8-14-12(13(19)5-6-15(19)18(23)24-3)4-7-16-20(14,2)11-9-17(22)21-16/h9,11-16H,4-8,10H2,1-3H3,(H,21,22)/t12-,13-,14-,15+,16+,19-,20+/m0/s1

Upstream product

• 67-56-1 methanol 
• 104239-97-6 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 17697-12-0 benzeneseleninic anhydride 
• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 
• 149198-45-8 methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate 

Downstream Products

• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 
• 1796930-46-5 dutasteride 
• 606101-78-4 2-Fluoro-4-methyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid methyl ester 
• 606101-79-5 (5α,17β)-2-Fluoro-3-oxo-4-methyl-4-azaandrost-1-ene-17-carboxylic acid 
• 104239-97-6 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 827589-62-8 Methyl 4-p-methoxybenzyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 
• 103335-44-0 Methyl 4-methyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide 
• 98319-26-7 finasteride 
• 496947-19-4 3-Oxo-4-phenyl-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 166896-63-5 Methyl 3-oxo-4-azaandrosta-1,5,7-triene-17β-carboxylate 
• 166896-62-4 Methyl 3-oxo-4-azaandrosta-1,5-diene-17β-carboxylate 
• 1026013-15-9 (4aR,4bS,6aS,7S,9aS,9bS)-11a-Methoxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid methyl ester 
• 138689-15-3 (5α,17β)-N-Methoxy-N-methyl-3-oxo-4-aza-androst-1-ene-17β-carboxamide 

Relevant articles and documents

A method of preparation he male amine

The invention belongs to the field of pharmaceutical chemistry, and relates to a high-yield method for preparing dutasteride, which comprises the following steps: (1) under the action of a catalyst, reacting aza-5-androst-1-alkenyl-3-keto-17beta-carboxylic acid (I) with alcohol to generate 4-aza-5-androst-1-alkenyl-3-keto-17beta-carboxylate (II); and (2) in the presence of a catalyst, reacting the 4-aza-5-androst-1-alkenyl-3-keto-17beta-carboxylate (II) with 2,5-ditrifluoromethylaniline in an organic solvent at certain reaction temperature to obtain the dutasteride (III) at high yield. The method has the characteristics of accessible raw material, mild reaction conditions and high product yield, and is easy to control.

PROCESS FOR PREPARING ANDROSTENONE DERIVATIVES

Provided is a process for preparing androstenone derivatives, specifically 3-oxo-4-aza-5α-androstene-17β-carboxylic acid of Formula I, a key intermediate for dutasteride.

Method of prevention of prostatic carcinoma with 17β-N-monosubstituted-carbamoyl-4-aza-5α-androst-1-en-3-ones

17β-N-monosubstituted-carbamoyl-4-aza-5α-androst-1-en-3-ones of the formula wherein R1is selected from hydrogen, methyl and ethyl and R2is a straight or branched chain alkyl, cycloalkyl, aralkyl of from 1-12 carbons, or monocyclic aryl optionally containing 1 or more lower alkyl substituents of 1-2 carbon atoms and/or 1 or more halogens, and R′, R″, R″′ are hydrogen or methyl are useful for the prevention of prostatic carcinoma.