138689-15-3

Basic information

• Product Name: (5α,17β)-N-Methoxy-N-Methyl-3-oxo-4-azaandrost-1-ene-17-carboxaMide
• Synonyms: (5α,17β)-N-Methoxy-N-Methyl-3-oxo-4-azaandrost-1-ene-17-carboxaMide
• CAS NO: 138689-15-3
• Molecular Formula: C₂₁H₃₂N₂O₃
• Molecular Weight: 360.49038
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 138689-15-3.mol

Chemical Properties

• Appearance: /
• Density: 1.121±0.06 g/cm3(Predicted)
• PKA: 14.15±0.70(Predicted)
• CAS DataBase Reference: (5α,17β)-N-Methoxy-N-Methyl-3-oxo-4-azaandrost-1-ene-17-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (5α,17β)-N-Methoxy-N-Methyl-3-oxo-4-azaandrost-1-ene-17-carboxaMide(138689-15-3)
• EPA Substance Registry System: (5α,17β)-N-Methoxy-N-Methyl-3-oxo-4-azaandrost-1-ene-17-carboxaMide(138689-15-3)

Safety Data

• Hazardous Substances Data: 138689-15-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5α,17β)-N-Methoxy-N-Methyl-3-oxo-4-azaandrost-1-ene-17-carboxaMide is used as an intermediate in the preparation of 5α-reductase inhibitors for the pharmaceutical industry. These inhibitors are essential in the treatment of various conditions, such as benign prostatic hyperplasia (BPH) and androgenetic alopecia (male pattern baldness). By targeting the 5α-reductase enzyme, these inhibitors help regulate the conversion of testosterone to dihydrotestosterone (DHT), which is responsible for the growth of prostate tissue and hair follicle miniaturization.

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 103335-41-7 methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 

Downstream Products

• 134067-56-4 17β-(phenylcarbonyl)-4-aza-5α-androst-1-ene-3-one 

Relevant articles and documents

Substituted 4-aza-5α-androstan-ones as 5α-reductase inhibitors

Described are new 16-substituted and 7,16-disubstituted 4-aza-5α-androstan-3-ones and related compounds as 5α-reductase inhibitors.

Delta-17 and delta-20 olefinic and saturated 17 beta-substituted 4-aza-5 alpha-androstan-ones as 5 alpha reductase inhibitors useful in the prevention and treatment of hyperandrogenic disorders

Described are delta 17 and delta 20 olefinic and saturated 17 Beta-substituted 4-aza-5 alpha-androstan-3-ones and related compounds having 5 alpha reductase inhibitors for treatment of benign prostatic hyperplasia and other hyperandrogenic related disorders.

A new general method for preparation of N-methoxy-N-methylamides. Application in direct conversion of an ester to a ketone

The reaction of an ester with N,O-dimethylhydroxylamine and a suitable organomagnesium reagent or lithium amide base provides a general method for the preparation of N-methoxy-N-methylamides. Application in the direct conversion of a highly hindered ester to a ketone, the azasteroid 5α-reductase inhibitor MK-0434, is described.

New process for making 3-oxo-4-aza-androst-1-ene 17beta-ketones

Described is a new process for preparing 3-oxo-4-aza-androst-1-ene 17β-ketones. The process involves converting the corresponding 17β-alkyl carboxylate to the N-methoxy-N-methyl carboxamide and reacting this with an appropriate Grignard reagent to form the desired ketone. The reaction can be conducted in "one pot", thus eliminating isolation of intermediates and avoiding the use of less stable intermediates, e.g., acid chlorides, acyl imidazolides and the like.

Intermediate for making 3-oxo-4-aza-androst-1-ene 17β-ketones

Described is a new intermediate and new process for preparing 3-oxo-4-aza-androst-1-ene 17β-ketones. The process involves converting the corresponding 17β-alkyl carboxylate to the N-methoxy-N-methyl carboxamide and reacting this with an appropriate Grignard reagent to form the desired ketone. The reaction can be conducted in "one pot", thus eliminating isolation of intermediates and avoiding the use of less stable intermediates, e.g., acid chlorides, acyl imidazolides and the like. The intermediate has the formula: STR1 wherein R1 is hydrogen.