5,8-DibroMoiMidazo[1,2-a]pyrazine
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![5,8-DibroMoiMidazo[1,2-a]pyrazine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220811/c96f426d969946dcab68b57589c0c8e7.png "5,8-DibroMoiMidazo[1,2-a]pyrazine")
5,8-DibroMoiMidazo[1,2-a]pyrazine
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CAS No:
957344-74-0
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Formula:
C6H3Br2N3
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Chemical Name:
5,8-DibroMoiMidazo[1,2-a]pyrazine
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Synonyms:
5,8-dibromoimidazo[1,2-a]pyrazine;5,8-Dibromo-imidazo[1,2-a]pyrazine;SCHEMBL274851;CTK5H8145;DTXSID10704845;KS-00000OS7;6535AC;ANW-61950;KM3372;MFCD13193554
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CAS No:
5,8-DibroMoiMidazo[1,2-a]pyrazine Use and Manufacturing
3, 6-dibromopyrazin-2-ylamine (4.0 g, 15.80 mmol) and bromoacetaldehyde diethyl acetal (3.7 mL, 24.00mmol) and tetrahydrofuran (5.3 mL) eere dissolved in distilled water (53 mL), the mixture was stirred for 4 hours at 120°C .Saturated aqueous sodium hydrogen carbonate solution to the reaction solution was neutralized by addition. The resulting solid was filtered and washed with distilled water and dried to give the title compound (2.75 g).A mixture of 5, 8-dibromoimidazo[l, 2-a]pyrazine (276 mg, 1.00 mmol), tert-butyl 4-[(5- bromothiazolo[5, 4-d]thiazol-2-yl)-methyl-amino]piperidine-l-carboxylate (108 mg, 0.25 mmol), prepared in Example 11, Pd(PPh3)4 (35 mg, 0.030 mmol), and hexabutylditin (0.38 mL, 0.73 mmol) in l, 4-dioxane (2.0 mL) was stirred at 100 C under argon overnight. After cooling, the solvent was removed and the residue was chromatographed on a silica gel column (ethyl acetate in dichloromethane, 0-100%) to provide a mixture of desired product which was further purified on a C- 18 column (acetonitrile in water, 0 -100%) to provide two isomers of coupling product, tert-butyl 4-[[2-(5-bromoimidazo[l, 2-a]pyrazin-8-yl)thiazolo[5, 4-d]thiazol-5-yl]-methyl- amino]piperidine-l-carboxylate (10 mg, 7.4%). LC-MS 550.1, 552.1 [M+H]+, RT 1.61 min., and tert-butyl 4-[[2-(8-bromoimidazo[l, 2-a]pyrazin-5-yl)thiazolo[5, 4-d]thiazol-5-yl]-methyl- amino]piperidine-l-carboxylate (2.8 mg, 2.0%). LC-MS 550.1, 552.1 [M+H]+, RT 1.68 min..To a solution of 8-bromo-5-chloro-imidazo[l, 2-c]pyrimidine (200 mg, 860 mhio) and 2-ami noacetamide (95 6 mg, 1.29 mmol) in CIECN (3 ml.) was added DIEA (556 mg, 4.3 mmol, 749 mE). The mixture was stirred at 50 C for 0.5 h. The reaction mixture was filtered affording 2-[(8-bromoimidazo[l , 2-c]pyrimidin-5-yl)amino]acetamide (210 mg, 778 miho, 90% yield) as a white solid. LCMS (ESI): m/z: [M +H] calculated for CsHgBrNsQ: 268.99, 271.99; found 270.1, 272.1.
Computed Properties
Molecular Weight:276.92
XLogP3:2.7
Hydrogen Bond Acceptor Count:2
Exact Mass:276.86732
Monoisotopic Mass:274.86937
Topological Polar Surface Area:30.2
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5,8-DibroMoiMidazo[1,2-a]pyrazine
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