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藥物詳細合成路線

Name Quazepam;Sch-161;Sch-16134;Oniria;Doral;Quazium;Selepam;Prosedar;Dormalin;Cetrane
Chemical Name 7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-1-(2,2,2-trifluoroethyl)-2H-1,4-benzodiazepine-2-thione
CAS 36735-22-5
Related CAS
Formula C17H11ClF4N2S
Structure
Formula Weight 386.80122
Stage 上市-1985
Company Schering-Plough (Originator), MedPointe (Licensee), Mitsubishi Pharma (Licensee), SSP (Licensee)
Activity/Mechanism PSYCHOPHARMACOLOGIC DRUGS, Sedative/Hypnotics, Sleep Disorders, Treatment of, Benzodiazepines, GABA(A) BZ Site Receptor Agonists
Syn. Route 2
Route 1
the alkylation of 2-amino-5-chloro-2-fluorobenzophenone (ii) with 2,2,2-trifluoroethyl trichloromethylsulfonate (a) gives 2-(2,2,2-trifluoroethylamino)-5-chloro-2-fluorobenzophenone (iii), which is bromoacetylated with bromoacetyl chloride (b) in refluxing benzene yielding the bromoacetanilide (iv).this compound is cyclized with nh3 in chloroform affording 7-chloro-1-(2,2,2-trifluoroethyl)-1,3-dihydro-5-(2-fluorophenyl)-2h-1,4-benzodiazepin-2-one (i), which by reaction with p2s5 in refluxing dioxane gives the target compound.
List of intermediates No.
5-[2-(dibenzylamino)acetyl]-2-hydroxybenzamide; 5-(n,n-dibenzylglycyl)salicylamide (b)
2-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1h-purin-8-yl)phenoxy]acetic acid (ii)
(1e,3s)-1-[2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-thiazol-4-yl]-2-methyl-1,5-hexadien-3-ol (i)
(1s)-1-[(e)-2-[2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-thiazol-4-yl]-1-methylethenyl]-3-butenyl (3s,6r,7s,8s)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-5-oxo-12-tridecenoate (iii)
(4s,7r,8s,9s,16s)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-16-[(e)-2-[2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-thiazol-4-yl]-1-methylethenyl]-5,5,7,9-tetramethyloxa-13-cyclohexadecene-2,6-dione (iv)
4-bromobenzoyl chloride (a)
Reference 1:
    steinman, m.; benzodiazepines and the process for their manufacture. de 2138773; es 393953; fr 2102114; gb 1345938 .
Reference 2:
    steinman, m.; 1-polyfluoroalkyl-1,4-benzodiazepin-2-thiones for effecting tranquilization, sedation and treating colvulsions. us 3920818 .
Reference 3:
    castaner, j.; thorpe, p.; quazepam. drugs fut 1978, 3, 2, 139.
Reference 4:
    topliss, j.g.; steinman, m.; alekel, r.; wong, y.s.; york, e.e.; 1-polyfluoroalkylbenzodiazepines. j med chem 1973, 16, 12, 1354-60.

Route 2
the alkylation of p-chloroaniline (v) as before yields n-(2,2,2-trifluoroethyl)aniline (vi), which is then condensed with aziridine (c) affording the substituted aniline (vii). the benzoylation of (vii) with 2-fluorobenzoyl chloride (d) yields the amide (viii), which is cyclized with p2o5 in refluxing pocl3 giving 7-chloro-(2,2,2-trifluoroethyl)-1,3-dihydro-2h-5-(2-fluorophenyl)-1,4-benzodiazepine (ix). this compound is oxidized with ruo4 in ccl4 to give 7-chloro-1-(2,2,2-trifluoroethyl)-1,3-dihydro-5-(2-fluorophenyl)-2h-1,4-benzodiazepin-2-one (i), which by reaction with p2s5 in refluxing dioxane gives the target compound.
List of intermediates No.
allyl (1r)-1-[(2r,3s)-2-(tert-butylsulfonyl)-4-oxoazetidinyl]ethyl carbonate (c)
2-azido-1-ethanol (v)
1h-imidazole-4,5-dicarboxylic acid (d)
(1e,3s)-1-[2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-thiazol-4-yl]-2-methyl-1,5-hexadien-3-ol (i)
4-bromobenzoyl chloride (a)
4-bromo-n-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzamide (vi)
3-(4-bromo-3-methylphenyl)-5-methyl-1,2,4-oxadiazole (vii)
(viii)
4-[[4-methoxy-3-(4-methyl-1-piperazinyl)anilino]carbonyl]phenylboronic acid (ix)
Reference 1:
    steinman, m.; benzodiazepines and the process for their manufacture. de 2138773; es 393953; fr 2102114; gb 1345938 .
Reference 2:
    steinman, m.; 1-polyfluoroalkyl-1,4-benzodiazepin-2-thiones for effecting tranquilization, sedation and treating colvulsions. us 3920818 .
Reference 3:
    castaner, j.; thorpe, p.; quazepam. drugs fut 1978, 3, 2, 139.
Reference 4:
    topliss, j.g.; steinman, m.; alekel, r.; wong, y.s.; york, e.e.; 1-polyfluoroalkylbenzodiazepines. j med chem 1973, 16, 12, 1354-60.

全民突击安卓跟苹果系统可以PK吗 www.uxeea.icu 來源:藥化網

作者:藥化小編

摘要:本文合成路線介紹的是藥物中文名夸西泮;英文名Quazepam;Sch-161;Sch-16134;Oniria;Doral;Quazium;Selepam;Prosedar;Dormalin;Cetrane;CAS[36735-22-5]

 
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