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Process for preparing dutasteride

A preparation process, a technology for dutasteride, which is applied in the technological field of dutasteride preparation, can solve the problems of unqualified product quality, difficult removal of pyridine, strong irritation and the like, and achieves good product quality, low toxicity, Equipment with less corrosive effect

Inactive Publication Date: 2013-08-21
青岛富康化工科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, the environmentally unfriendly pyridine is used as a reaction solvent or as an acid-binding agent in the amidation process. Pyridine is highly irritating and can anesthetize the central nervous system, causing certain hazards to operators.
At the same time, pyridine is not easy to remove, and it is easy to cause unqualified product quality.

Method used

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  • Process for preparing dutasteride
  • Process for preparing dutasteride
  • Process for preparing dutasteride

Examples

Experimental program
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Effect test

Embodiment 1

[0032] The synthesis of embodiment 1 formula (2) compound

[0033] Dissolve 10 grams of the compound of formula (1) in 100 ml of toluene, add 10 grams of dichlorodicyanobenzoquinone, add 20 ml of N, O-bis(trimethylsilyl) trifluoroacetamide dropwise at room temperature, and drop at room temperature React for 12 hours, then heat up to 125°C and react for 18 hours, cool to room temperature, spin off toluene, add 145ml of dichloromethane and 100ml of 1% sodium bisulfite aqueous solution, stir well, filter, separate the organic phase, and successively wash with 2M hydrochloric acid Wash twice, wash twice with saturated sodium chloride, decolorize with activated carbon for 1 hour, filter with suction, spin off the solvent, and recrystallize from acetonitrile to obtain 5.2 g of compound (2).

[0034] ESI-MS m / z: 316.2 [M-H] - ; 1 H-NMR (DMSO-d 6 )δ0.63(s, 3H), 0.85(s, 3H), 0.97-1.00(m, 2H), 1.10-1.15(m, 1H), 1.16-1.29(m, 3H), 1.31-1.44(m, 2H), 1.57-1.66(m, 3H), 1.67-1.74(m, 1H), ...

Embodiment 2

[0035] Embodiment 2, the synthesis of formula (3) compound dutasteride

[0036] Dissolve 5.0 g of the compound of formula (2) in 50 ml of toluene, add 1 ml of N,N-dimethylformamide, add 1.5 g of solid triphosgene in batches under ice-bath conditions, and react at 55°C for 2 hours. Cool to room temperature, add 3.33 g of solid sodium carbonate, then add 4.0 g of 2,5-bis(trifluoromethyl)aniline, raise the temperature to 115°C, react for 12 hours, cool to room temperature, filter with suction, and wash the filtrate with water successively 2 times, 2M hydrochloric acid washing 2 times, saturated sodium carbonate washing 2 times, saturated saline washing 2 times, activated carbon decolorization for 1 hour, suction filtration, spin-drying solvent, ethyl acetate recrystallization, acetonitrile recrystallization to obtain dutasteride (3) 7.2 grams. Yield 86.8%, melting point: 246-248; ESI-MS m / z: 529.3[M+H] + ; 1 H-NMR (DMSO-d 6)δ0.66(s, 3H), 0.87(s, 3H), 0.98-1.03(m, 2H), 1.17-1....

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Abstract

The invention discloses a process for preparing dutasteride, and belongs to the field of pharmaceutical chemical synthesis. The process comprises the following steps: carrying out 1,2-position dehydrogenation on a compound shown in a formula (1) so as to obtain a compound shown in a formula (2); and after the compound shown in the formula (2) is prepared into acyl chloride, carrying out amidation on the acyl chloride and 2,5-bis(trifluoromethyl)aniline so as to obtain dutasteride shown in a formula (3). The process disclosed by the invention is simple in operation, mild in reaction conditions, safe and reliable in production, high in reaction yield, low in cost, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to a preparation process of chemical medicines, in particular to a process for preparing dutasteride. Background technique [0002] Benign Prostate Hyperplasia (BPH) is one of the common and multiple diseases of middle-aged and elderly men. According to relevant domestic statistics, the incidence rate of men aged 50 is more than 50%, and the incidence rate can reach 90% when they are 80 years old. The main symptoms of benign prostatic hyperplasia are dysuria, frequent urination, slow start of urination, weak urinary stream, intermittent or dribbling, etc. What's more, acute urinary retention and filling incontinence may occur. Currently, finasteride and dutasteride are clinically used to treat benign prostatic hyperplasia. [0003] Dutasteride (Dutasteride, CAS: 164656-23-9), chemical name: (5α, 17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-keto-4- Aza-5α-androst-1-ene-17β-carboxylic acid amin...

Claims

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Application Information

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IPC IPC(8): C07J73/00
Inventor 宋伟国张晓攀宋成刚李书涛魏代宝陈长亮
Owner 青岛富康化工科技有限公司
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