166896-74-8

Basic information

• Product Name: 17b-(tert-Butylcarbamoyl)-4-aza-5a-androsten-3-one
• Synonyms: 17B-(TERT-BUTYLCARBAMOYL)-4-AZA-5A-ANDROSTEN-3-ONE;(17beta)-N-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-5-ene-17-carboxamide;N-t-Butyl-3-Oxo-4-Aza-5-Androsten-17β-Carboxamide;17-beta-(n-butylcarbaMoyl)-4-aza-5-alpha-androsten-3-one;17β-(t-Butylcarbamoyl)-4-aza-5α-androsten-3-one (F8);(1S,3aS,3bS,5aR,9aR,9bS)-N-tert-butyl-9a-methyl-7-oxo-2,3,3a,3b,4,5,5a,6,9b,10,11,11a-dodecahydro-1H-indeno[5,4-f]quinoline-1-carboxamide
• CAS NO: 166896-74-8
• Molecular Formula: C₂₃H₃₆N₂O₂
• Molecular Weight: 372.54
• Mol File: 166896-74-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 289-293 °C
• Boiling Point: 588.477 °C at 760 mmHg
• Flash Point: 182.971 °C
• Appearance: /
• Density: 1.10
• Refractive Index: 1.523
• PKA: 15.44±0.70(Predicted)
• CAS DataBase Reference: 17b-(tert-Butylcarbamoyl)-4-aza-5a-androsten-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 17b-(tert-Butylcarbamoyl)-4-aza-5a-androsten-3-one(166896-74-8)
• EPA Substance Registry System: 17b-(tert-Butylcarbamoyl)-4-aza-5a-androsten-3-one(166896-74-8)

Safety Data

• Hazardous Substances Data: 166896-74-8(Hazardous Substances Data)

Usage

Uses

(4aR,4bS,6aS,7S,9aS,9bS)-N-(1,1-Dimethylethyl)-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide, is an impurity of Finasteride (F342000), Inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone.Antialopecia agent.

InChI:InChI=1/C22H34N2O2/c1-21(2,3)24-20(26)16-6-5-13-14(16)7-9-17-15(13)8-10-18-22(17,4)12-11-19(25)23-18/h11-18H,5-10H2,1-4H3,(H,23,25)(H,24,26)/t13-,14?,15+,16+,17+,18-,22-/m1/s1

Upstream product

• 57072-90-9 3-oxoandrost-4-ene-17β-carboxylic acid chloride 
• 131267-80-6 N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide 
• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 
• 190006-01-0 17β-(N-tert-butyl)-carbamoyl-5-oxo-A-nor-3,5-secoandrostane-3-oic acid 

Downstream Products

• 98319-26-7 finasteride 
• 98319-24-5 dihydro-finasteride 

Relevant articles and documents

A 3-carbonyl-4-aza-5-androstene -17 β method for preparing derivatives of

The invention provides a preparation method of a 3-carbonyl-4-aza-5-androstene-17beta derivative. The preparation method comprises the following steps: suspending an A-nor-3,5-cracking-androstan-5-keto-3-carboxylic acid-17beta derivative II in an aqueous solution of ammonium acetate for performing a ring-closure reaction; cooling a reaction product; adjusting the PH value of the reaction product by using industrial ammonia water; filtering the reaction product by spinning; drying the reaction product by spinning; and washing a filter cake by using water, and drying the filter cake to obtain a 3-carbonyl-4-aza-5-androstene-17beta derivative I, wherein R in a formula II and a formula I is carbonyl, carboxylic acid, carboxylic ester, amide, acetyl, hydroxyl, alkyl, ether or chloro. The preparation method has the advantages of mild reaction condition in the absence of inorganic solvents, low requirements on equipment and pre-treatment, complete reaction, and high product purity of over 99 percent without purification; moreover, a spinning-filtered mother solution is recovered, so that the emission of three wastes is reduced greatly; in the whole reaction, used raw materials are readily available; and meanwhile, the reaction yield is high, and the preparation method is economical and environmentally friendly, and is convenient for industrial implementation.

Synthesis of N-substituted 3-oxo-17β -carboxamide-4-aza-5α-androstanes and the tautomerism of 3-oxo-4-aza-5-androstenes

An N-aryl-3-oxo-4-aza-5α -androst-1-ene-17β carboxamide and three N-aryl or alkyl substituted 17α -hydroxy-3-oxo-4-aza-5α -androstane-17β -carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17β - carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.