N,N-diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide

Base Information

• Chemical Name: N,N-diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide
• CAS No.: 92472-70-3
• Molecular Formula: C23H36 N2 O2
• Molecular Weight: 372.551
• Mol file: 92472-70-3.mol

Synonyms:4-Azaandrost-1-ene-17-carboxamide,N,N-diethyl-3-oxo-, (5a,17b)-; 1H-Indeno[5,4-f]quinoline,4-azaandrost-1-ene-17-carboxamide deriv.; 17b-N,N-Diethylcarbamoyl-4-aza-5a-androst-1-en-3-one

Chemical Property of N,N-diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide

Chemical Property:

• Vapor Pressure: 4.14E-12mmHg at 25°C
• Boiling Point: 549.1°Cat760mmHg
• Flash Point: 285.9°C
• PSA: 56.01000
• Density: 1.07g/cm³
• LogP: 3.91400

Purity/Quality:

N,N-Diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N,N-Diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide due to its azasteriod struture has been studied as a human 5α-?reductase inhibitors.

Technology Process of N,N-diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide

There total 13 articles about N,N-diethyl-3-oxo-4-azaandrost-1-ene-17-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

N,N-diethyl-3-oxo-4-aza-5α-androstane-17β-carboxamide (73671-87-1) → N,N-diethyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide (92472-70-3)

Guidance literature:

With benzeneseleninic anhydride; In diethylene glycol dimethyl ether; at 120 ℃; for 19h;

DOI:10.1021/jm00378a028

Reference yield:

androst-4-en-3-one-17β-carboxylic acid (302-97-6) → N,N-diethyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide (92472-70-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) pyridine, oxalyl chloride / 1.) toluene, RT, 1 h, 2.) toluene, 0.5 h

2: 87 percent / Na₂CO₃, NaIO₄, KMnO₄ / 2-methyl-propan-2-ol; H₂O / Heating

3: NH₃ / ethanol / 8 h / 180 °C

4: H₂ / PtO₂ / acetic acid / 3 h / 25 - 60 °C / 2327.2 Torr

5: 1.) dimethyl sulfate, 2.) K₂CO₃ / 1.) CHCl₃, reflux, 5 h

6: 1.) LDA / 1.) THF, -78 to 0 deg C, 5 min, 2.) THF

7: 67 mg / NaIO₄ / methanol; H₂O / 2.5 h

8: toluene / 2.5 h / Heating

With pyridine; potassium permanganate; sodium periodate; oxalyl dichloride; ammonia; hydrogen; sodium carbonate; potassium carbonate; dimethyl sulfate; lithium diisopropyl amide; platinum(IV) oxide; In methanol; ethanol; water; acetic acid; toluene; tert-butyl alcohol;

DOI:10.1021/jm00378a028

Reference yield:

Pregnenolone (145-13-1) → N,N-diethyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide (92472-70-3)

Guidance literature:

Multi-step reaction with 12 steps

1: I₂ / 1 h / Heating

2: methanol / 1 h / Heating

3: 1.) Al(i-PrO)3, 2.) Supercel, Darco KB / 1.) toluene, cyclohexanone, reflux, 1 h, 2.) toluene, cyclohexanone, water, 15 min

4: 1.71 kg / 10percent KOH / methanol / Heating

5: 1.) pyridine, oxalyl chloride / 1.) toluene, RT, 1 h, 2.) toluene, 0.5 h

6: 87 percent / Na₂CO₃, NaIO₄, KMnO₄ / 2-methyl-propan-2-ol; H₂O / Heating

7: NH₃ / ethanol / 8 h / 180 °C

8: H₂ / PtO₂ / acetic acid / 3 h / 25 - 60 °C / 2327.2 Torr

9: 1.) dimethyl sulfate, 2.) K₂CO₃ / 1.) CHCl₃, reflux, 5 h

10: 1.) LDA / 1.) THF, -78 to 0 deg C, 5 min, 2.) THF

11: 67 mg / NaIO₄ / methanol; H₂O / 2.5 h

12: toluene / 2.5 h / Heating

With pyridine; potassium hydroxide; potassium permanganate; sodium periodate; oxalyl dichloride; ammonia; hydrogen; iodine; silica gel; aluminum isopropoxide; sodium carbonate; potassium carbonate; pyrographite; dimethyl sulfate; lithium diisopropyl amide; platinum(IV) oxide; In methanol; ethanol; water; acetic acid; toluene; tert-butyl alcohol;

DOI:10.1021/jm00378a028

upstream raw materials:

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-7-(Imidazole-1-carbonyl)-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-indeno[5,4-f]quinolin-2-one

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-3-Benzenesulfinyl-4a,6a-dimethyl-2-oxo-hexadecahydro-indeno[5,4-f]quinoline-7-carboxylic acid diethylamide

N,N-diethyl-3-oxo-4-aza-5α-androstane-17β-carboxamide

Pregnenolone

Refernces

• 1、 Bhattacharya, Apurba,DiMichele, Lisa M.,Dolling, Ulf-H.,Douglas, Alan W.,Grabowski, Edward J. J.. "Silylation-Mediated Oxidation of 4-Aza-3-ketosteroids with DDQ Proceeds via DDQ-Substrate Adducts". . p. 3318 - 3319. Retrieved 2007/10/02.