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[ CAS No. 53052-06-5 ]

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Chemical Structure| 53052-06-5
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CAS No. :53052-06-5 MDL No. :MFCD01089040
Formula : C6H4N2OS Boiling Point : 284.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :152.17 g/mol Pubchem ID :658727
Synonyms :

Safety of [ 53052-06-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53052-06-5 ]

  • Upstream synthesis route of [ 53052-06-5 ]
  • Downstream synthetic route of [ 53052-06-5 ]

[ 53052-06-5 ] Synthesis Path-Upstream   1~8

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  • [ 60832-72-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 1, p. 167 - 170
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  • [ 16867-03-1 ]
  • [ 140-89-6 ]
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YieldReaction ConditionsOperation in experiment
86.95% at 110℃; Step 1: Preparation of oxazolo[4,5-b]pyridine-2-thiol A solution of 2-aminopyridin-3-ol (5.0g, 45.45 mmol) and potassium ethyl xanthate (8.0g, 49.99 mmol) in pyridine (50mL) was heated at 110°C overnight. The reaction mixture was cooled to 0°C, added ice water and acidified with Cone. HCl. The solid was filtered and dried under vacuum to afford the title compound (6.0g, 86.95percent). 1HNMR (DMSO-d6, 300MHz): δ 8.24-8.22 (d, 1H), 7.90-7.87 (d, 1H), 7.30-7.26 (m, 1H). LCMS: m/z: 153.0 (M+l) +.
86.95% at 110℃; A solution of 2-aminopyridin-3-ol (5.0 g, 45.45 mmol) and potassium ethyl xanthate (8.0 g, 49.99 mmol) in pyridine (50 mL) was heated at 1100 C. overnight. The reaction mixture was cooled to 00 C., added ice water and acidified with Conc. HC1. The solid was filtered and dried under vacuum to afford the title compound (6.0 g, 86.95percent). 10206] ‘HNMR (DMSO-d5, 300 MHz): ö 8.24-8.22 (d, 1H), 7.90-7.87 (d, 1H), 7.30-7.26 (m, 1H). LCMS: mlz:153.0 (M+1).
Reference: [1] Patent: WO2015/104688, 2015, A1, . Location in patent: Page/Page column 36
[2] Patent: US2016/340366, 2016, A1, . Location in patent: Paragraph 0205; 0206
[3] Monatshefte fur Chemie, 2011, vol. 142, # 9, p. 895 - 899
[4] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5721 - 5725
[5] European Journal of Medicinal Chemistry, 2005, vol. 40, # 1, p. 15 - 23
[6] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 1, p. 114 - 125
[7] Patent: EP1308439, 2003, A1,
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YieldReaction ConditionsOperation in experiment
67% With potassium hydroxide In ethanol for 10 h; Reflux In a 100 ml round bottom flask was placed 2- amino-3-hydroxy pyridine (2.20g, 20 mmol) and 40 ml of absoluteethanol was added and the mixture was stirred for 15minutes. In the meanwhile, 2.0g (29 mmol) KOH pelletswere powdered and transferred into the flask followed by theaddition of 15 ml of carbon disulfide. The resulting mixturewas refluxed over an oil bath for 8 hours when a yellowprecipitate appeared. The contents of the flask were cooledto room temperature. The solvent was rotary evaporated andthe residue was transferred in to a beaker and 75 ml of waterwas added followed by neutralization with acetic acid. Theprecipitated product was filtered under vacuum and washedwith 3x50 ml of water and dried under vacuum over night toyield 2.1g of light yellow solid product (yield, 65percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 2075 - 2078
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1837 - 1843
[3] Letters in Organic Chemistry, 2010, vol. 7, # 7, p. 519 - 527
[4] Archiv der Pharmazie, 2017, vol. 350, # 8,
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Reference: [1] Patent: US4351832, 1982, A,
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  • [ 137-26-8 ]
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Reference: [1] Green Chemistry, 2017, vol. 19, # 23, p. 5591 - 5598
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  • [ 53052-06-5 ]
  • [ 74-88-4 ]
  • [ 169205-95-2 ]
YieldReaction ConditionsOperation in experiment
93.75% With potassium carbonate In ethyl acetate at 20℃; Step 2: Preparation of 2-(methylthio)oxazolo[4,5-b]pyridine To a stirred solution of oxazolo[4,5-b]pyridine-2-thiol (3.0g, 19.73 mmol) in ethyl acetate (30mL) was added potassium carbonate (3.81g, 27.62 mmol) and methyl iodide (3.08g, 21.71 mmol) and stirred at RT overnight. The reaction mixture was diluted with water (100ml), extracted with ethyl acetate (2x50mL), dried over sodium sulphate and concentrated to afford the title compound (3.0g, 93.75percent). 1HNMR (CDCI3, 300MHz): δ 8.46-8.44 (d, 1H), 7.71-7.68 (d, 1H), 7.20-7.15 (m, 1H), 2.81 (s, 3H). LCMS: m/z: 167.0(M+1) +.
93.75% With potassium carbonate In ethyl acetate at 20℃; To a stirred solution of oxazolo[4,5-b]pyridine-2- thiol (3.0 g, 19.73 mmol) in ethyl acetate (30 mL) was added potassium carbonate (3.81 g, 27.62 mmol) and methyl iodide (3.08 g, 21.71 mmol) and stirred at RT overnight. The reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (2x50 mL), dried over sodium sulphate and concentrated to afford the title compound (3.0 g, 93 .75percent).10208] ‘HNMR (CDC13, 300 MHz): ö 8.46-8.44 (d, 1H),7.71-7.68 (d, 1H), 7.20-7.15 (m, 1H), 2.81 (s, 3H). LCMS:mlz: 167.0 (M+1)+.
Reference: [1] Patent: WO2015/104688, 2015, A1, . Location in patent: Page/Page column 36
[2] Patent: US2016/340366, 2016, A1, . Location in patent: Paragraph 0207; 0208
[3] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5721 - 5725
[4] Ultrasonics Sonochemistry, 2010, vol. 17, # 5, p. 783 - 788
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 2075 - 2078
[6] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1837 - 1843
[7] European Journal of Medicinal Chemistry, 2005, vol. 40, # 1, p. 15 - 23
[8] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 1, p. 114 - 125
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  • [ 53052-06-5 ]
  • [ 74-88-4 ]
  • [ 169205-95-2 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide for 2 h; 2-(Mβthv)thio)ri,31oxazolor4,5-biPyridine; A 250 mL RB flask, equipped with a magnetic stirring bar and nitrogen gas inlet, was charged with [1,3]oxazolo[4,5-b]pyridine-2(3H)-thione (5.00 g, 32.9 mmol), potassium carbonate (4.54 g, 32.8 mmol), and 80 mL of anhydrous DMF. Then iodomethane (2.45 mL, 5.57 g, 39.3 mmol) was added dropwise to the stirring reaction mixture under nitrogen. The mixture was stirring for 2 h, then diluted with 300 mL of water, and extracted with EtOAc (4x150 mL). The combined organic extract was washed with water (3x100 mL), then with brine (100 mL), dried over Na2SO4 and evaporated to give 4.53 g (83 percent) of 2- (methylthio)[1,3]oxazolo[4,5-b]pyridine as a tan solid. LCMS m/z (M+H): 167.1. 1H NMR (300 MHz, DMSO-d6): δ 8.44 (1H), 8.08 (1H), 7.35 (1H), 2.81 (3H).
Reference: [1] Patent: WO2006/51410, 2006, A1, . Location in patent: Page/Page column 45
[2] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
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Reference: [1] Chemistry of Heterocyclic Compounds, 1999, vol. 35, # 1, p. 84 - 86
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