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药物详细合成路线

Name Secnidazole;RP-14539;PM-185184;Flagentyl
Chemical Name alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol;1-(2-Hydroxypropyl)-2-methyl-5-nitroimidazole;1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol
CAS 3366-95-8
Related CAS
Formula C7H11N3O3
Structure
Formula Weight 185.18402
Stage 上市
Company Aventis Pharma (Originator)
Activity/Mechanism ANTIINFECTIVE THERAPY, Antitrichomonals, Treatment of Protozoal Diseases
Syn. Route 3
Route 1
the nitration of (i) with hno3 and h2so4 gives 2-methyl-4(5)-nitroimidazole (ii), which is then condensed with refluxing 1-chloroisopropanol (b) or with propylene oxide in 85% formic acid (a).
List of intermediates No.
(3ar,6as)-2-oxohexahydro-2h-cyclopenta[b]furan-4-carbaldehyde (i)
5-[4-[2-([[(e)-1-(6-phenyl-3-pyridinyl)ethylidene]amino]oxy)ethoxy]benzyl]-3-trityl-1,3-thiazolidine-2,4-dione (a)
ethyl (1r,2s,4r)-2-isopropenyl-1-methyl-4-vinylcyclohexanecarboxylate (ii)
[(1r,2s,4r)-2-isopropenyl-1-methyl-4-vinylcyclohexyl]methanol (b)
Reference 1:
    nouveaux derives de limidazole et compositions les contenant. fr 3270m .
Reference 2:
    cosar, c.; crisan, c.; horclois, r.; jacob, r.m.; robert, j.; tchelitcheff, s.; vaupre,r.; nitroimidazoles. arzneim-forsch drug res 1966, 16, 1, 23-29.
Reference 3:
    hillier, k.; secnidazole. drugs fut 1979, 4, 4, 280.

Route 2
the condensation of (i) with propylene oxide (a) in ethanol at 20 c gives 1-(2-hydroxypropyl)-2-methylimidazole (iii), which is acetylated with acetyl chloride in refluxing acetonitrile yielding the corresponding acetate (iv). the nitration of (iv) by means of hno3 and p2o5 affords 1-(2-acetoxypropyl)-2-methyl-4-nitroimidazole (v), which is finally hydrolyzed with 4n hcl at 90 c.
List of intermediates No.
(3ar,6as)-2-oxohexahydro-2h-cyclopenta[b]furan-4-carbaldehyde (i)
5-[4-[2-([[(e)-1-(6-phenyl-3-pyridinyl)ethylidene]amino]oxy)ethoxy]benzyl]-3-trityl-1,3-thiazolidine-2,4-dione (a)
1-[(1r,3s,4r)-4-(hydroxymethyl)-3-isopropenyl-4-methylcyclohexyl]-1-ethanone (iii)
(1r,2s,4r)-4-acetyl-2-isopropenyl-1-methylcyclohexanecarbaldehyde (iv)
methyl (1s,2s,3s,4r)-3-[(1s)-1-amino-2-ethylbutyl]-4-[(tert-butoxycarbonyl)amino]-2-hydroxycyclopentanecarboxylate (v)
Reference 1:
    cosar, c.; crisan, c.; horclois, r.; jacob, r.m.; robert, j.; tchelitcheff, s.; vaupre,r.; nitroimidazoles. arzneim-forsch drug res 1966, 16, 1, 23-29.
Reference 2:
    jeanmart, c.; messer, m. (aventis pharma sa); new process for the preparation of 5-nitroimidazole derivatives. de 2107405; fr 2079880; gb 1278757; jp 49080066 .
Reference 3:
    hillier, k.; secnidazole. drugs fut 1979, 4, 4, 280.

Route 3
the reaction of (i) with chloroacetone (c) by means of k2co3 in refluxing acetone gives (2-methylimidazol-1-yl)acetone (vi), which is nitrated with hno3 and p2o5 affording the corresponding nitro compound (vii). finally, this product is reduced with nabh4 in methanol at room temperature.
List of intermediates No.
(2r)-2-amino-3-methyl-1-butanol; (r-(-))-valinol; d-valinol (c)
(3ar,6as)-2-oxohexahydro-2h-cyclopenta[b]furan-4-carbaldehyde (i)
methyl (1s,2s,3s,4r)-3-[(1s)-1-(acetamido)-2-ethylbutyl]-4-[(tert-butoxycarbonyl)amino]-2-hydroxycyclopentanecarboxylate (vi)
methyl (1s,2s,3r,4r)-3-[(1s)-1-(acetamido)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate (vii)
Reference 1:
    cosar, c.; crisan, c.; horclois, r.; jacob, r.m.; robert, j.; tchelitcheff, s.; vaupre,r.; nitroimidazoles. arzneim-forsch drug res 1966, 16, 1, 23-29.
Reference 2:
    jeanmart, c.; messer, m. (aventis pharma sa); process for the preparation of 5-nitroimidazole derivatives. ch 513177; de 2107423; fr 2079879; gb 1278758; nl 7101641 .
Reference 3:
    hillier, k.; secnidazole. drugs fut 1979, 4, 4, 280.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名塞克硝唑;英文名Secnidazole;RP-14539;PM-185184;Flagentyl;CAS[3366-95-8]

 
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