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3-(4-(2-aMinoethylaMino)-1,2,5-oxadiazol-3-yl)-4-(3-broMo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide synthesis
- Product Name:3-(4-(2-aMinoethylaMino)-1,2,5-oxadiazol-3-yl)-4-(3-broMo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide
- CAS Number:1204669-57-7
- Molecular formula:C12H11BrFIN6O3
- Molecular Weight:513.061
![1,2,4-Oxadiazol-5(4H)-one, 3-[4-[(2-azidoethyl)amino]-1,2,5-oxadiazol-3-yl]-4-(3-bromo-4-fluorophenyl)-](/CAS/20180703/GIF/1204669-66-8.gif)
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![3-(4-(2-aMinoethylaMino)-1,2,5-oxadiazol-3-yl)-4-(3-broMo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide](/CAS/20150408/GIF/1204669-57-7.gif)
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Yield:1204669-57-7 95 g
Reaction Conditions:
with chloro-trimethyl-silane;sodium iodide in methanol at 20 - 42; for 1 h;
Steps:
22.I Step I:
3-(4-(2-aminoethylamino)-1,2,5-oxadiazol-3-yl)-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide
3-(4-(2-azidoethylamino)-1,2,5-oxadiazol-3-yl)-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (80.0 g, 0.194 mol) was mixed with methanol (800 mL).
Sodium iodide (175.0 g, 1.17 mol) was added.
The reaction was stirred at room temperature for 10 min.
Chlorotrimethylsilane (148 mL, 1.17 mol) was dissolved in methanol (100 mL) and added to the reaction over 30 min.
The reaction temperature rose 42° C.
The reaction was stirred at room temperature for 30 min LCMS indicated reaction completed (M+H=386).
The reaction was quenched with sodium thiosulfate (190.0 g, 1.20 mol) in water (900 mL).
A large amount of solid precipitated.
The product was collected by filtration (filtration speed was slow), rinsed with water (200 mL), and dried on vacuum overnight.
The filter cake was slurried in ethyl acetate (500 mL) for 30 min.
References:
US9320732,2016,B2 Location in patent:Page/Page column 90; 91
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![3-(4-(2-aMinoethylaMino)-1,2,5-oxadiazol-3-yl)-4-(3-broMo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one hydroiodide](/CAS/20150408/GIF/1204669-57-7.gif)
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