103335-55-3Relevant articles and documents
A synthetic 3-carbonyl-4-nitrogen mixed male steroid -17 β derivative method
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Paragraph 0056-0065, (2017/01/26)
The invention discloses a method for synthesizing 3-carbonyl-4-azaandrost-17beta derivative I, which comprises the following steps: (1) in the presence of an acidic catalyst, dissolving A-norandrostane-3,5-cracked-androst-5-one-3-carboxylic acid-17beta derivative II in dioxane aqua ammonia, heating, and slowly and dropwisely adding reducer-dissolved aqua ammonia to simultaneously perform reduction amination reaction and ring-closing reaction; (2) adding acid to destroy the reducer, concentrating under normal pressure, and recovering dioxane; (3) cooling, and carrying out centrifugal filtration to obtain a filter cake; washing the filter cake with water to a neutral state, and carrying out centrifugal drying to obtain a 3-carbonyl-4-azaandrost-17beta derivative I crude product; and (4) pulping the 3-carbonyl-4-azaandrost-17beta derivative I crude product with methanol, carrying out centrifugal filtration to obtain a filter cake, washing the filter cake with methanol, carrying out centrifugal drying, and baking to obtain the 3-carbonyl-4-azaandrost-17beta derivative refined product. By completing the reduction amination reaction and ring-closing reaction in one step, the method has the advantages of low reaction temperature, high product yield and good product quality, is economical and environment-friendly, and is suitable for industrialization.
PROCESS FOR THE SYNTHESIS OF (5α,17β)-N-[(2,5-BIS(TRIFLUOROMETHYL)-PHENYL]-3-OXO-4-AZA-5-ANDROST-1-ENE-17-CARBOXAMIDE
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, (2013/03/26)
The synthesis consists of reaction steps as follows: oxidizing the α,β-unsaturated ketone system of ring "A" of pregn-4-ene-3,20-dion- of formula (II) with sodium metaperiodate in tert-butanol in the presence of potassium permanganate and alkali metal carbonate, reacting the obtained 3,5-seco acid with an ester of chloroformic acid in the presence of tertier organic base below 0°C, reacting the obtained new compound after isolation or without isolation with ammonia or ammonium acetate, cyclization of the resulting carboxamides with an acid, cathalytic hydrogenating the obtained ene lactame, and oxidizing the side chain at position 17 of the obtained pregnane compound with an alkali metal hypobromide in aqueous dioxane below 10°C. Thereafter on one hand the obtained (5α,17β)-3-oxo-4-aza-5-androstane-17-carboxylic acid is reacted with chloroformic acid ester, the obtained new compound is reacted with 2,5-bis(trifluoromethyl)-aniline in the presence of a Lewis acid, the obtained amide is reacted with trimethyl chlorosilane in inert atmosphere in the presence of Ν,Ν,Ν',Ν'-tetramethyl-ethylendiamine, then en excess iodine is added to the reaction mixture and the product of the iodination reaction is crystallized from acetonitrile, then the obtained 2-iodo-3-oxo-4-aza-17β-carboxamide is reacted with potassium tert-butylate to furnish final product. On the other hand, (5α,17β)-3-oxo-4-aza-5-androstane-17-carboxylic acid is transformed into methylester by known method, this latter is transformed into methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate according to known method, the obtained compound is reacted with potassium-tert-butylate, the obtained (5α,17β)-3-oxo-4-aza-5-androst-1-ene-17-carboxylic acid is reacted with an ester of chloroformic acid, then the obtained new compound is coupled with 2,5-bis(trifluoromethyl)-aniline in the presence of a Lewis acid catalyst to gain final product.
METHOD FOR THE SELECTIVE PREPARATION OF 3-OXO-4-AZA-5A-ANDROSTANE COMPOUND
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Page 7, (2008/06/13)
This invention relates to a method for selectively preparing the 3-oxo-4-aza-5￥á-androstane compound which is used as an intermediate of finasteride by heating 3-oxo-4-aza-5-androstene in a mixture of formic acid and an alkanediol in the presence of zinc.
