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[ CAS No. 166266-19-9 ]

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2D
Chemical Structure| 166266-19-9
Chemical Structure| 166266-19-9
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Product Details of [ 166266-19-9 ]

CAS No. :166266-19-9MDL No. :MFCD02102422
Formula : C6H7IN2 Boiling Point : 303.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :234.04Pubchem ID :959586
Synonyms :

Computed Properties of [ 166266-19-9 ]

TPSA : 38.9 H-Bond Acceptor Count : 2
XLogP3 : 1.5 H-Bond Donor Count : 1
SP3 : 0.17 Rotatable Bond Count : 0

Safety of [ 166266-19-9 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 166266-19-9 ]

  • Upstream synthesis route of [ 166266-19-9 ]
  • Downstream synthetic route of [ 166266-19-9 ]

[ 166266-19-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 166266-19-9 ]
  • [ 59782-89-7 ]
Reference: [1] Patent: US6372766, 2002, B1,
  • 2
  • [ 166266-19-9 ]
  • [ 65550-78-9 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 16, p. 5356 - 5359
  • 3
  • [ 3430-21-5 ]
  • [ 166266-19-9 ]
YieldReaction ConditionsOperation in experiment
93% With copper(l) iodide; 2,3-dimethyl-2,3-diaminobutane; sodium iodide In 1,4-dioxane at 110℃; To dioxane (10 mL) was added 5-bromo-3-methylpyridin-2-amine (2 g, 10.6 mmol), sodium iodide (3.2 g, 21.4 mmoL), copper iodide (0.190 g, 1.06 mmol) and the solution degassed followed by addition of tetramethylethane-1,2-diamine (0.803 mL, 1.06 mmol) this mixture heated at 110° C. overnight. After cooling water was added and extracted the crude product with ethyl acetate. The residue was purified by column chromatography to give 5-iodo-3-methylpyridin-2-amine as a beige solid (2.3 g, 93percent). Analogous to the procedure described in Ex. 40, 6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.100 g, 0.51 mmol) and 5-iodo-3-methylpyridin-2-amine (0.119 g, 0.53 mmol) were coupled to yield pure 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.020 g, 13percent) after reverse phase HPLC purification. ES-MS (M+H)+=303. Analogous to the sulfonylurea urea formation described in Ex 5, 3-(6-amino-5-methylpyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.010 g, 0.034 mmol) and (5-Chloro-thiophene-2-sulfonyl)-carbamic acid ethyl ester (0.048 g, 0.166 mmol) were coupled to give 1-(5-chlorothiophen-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)-3-methylpyridin-2-yl)urea (0.016 g, 85percent). RP-HPLC: 2.7 min; ES-MS (M+H)+=526.0; 1H-NMR (DMSO-d6) δ (ppm): 2.2 (s, 3), 2.8 (s, 3), 5.6 (s, 2), 6.2 (d, 1), 6.8 (bs, 1), 7.2 (s, 1), 7.4 (d, 1), 7.6 (s, 1), 7.8 (d, 1), 8.2 (d, 1), 9.6 (bs, 1).
Reference: [1] Patent: US2006/69093, 2006, A1, . Location in patent: Page/Page column 23
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  • [ 1603-40-3 ]
  • [ 166266-19-9 ]
YieldReaction ConditionsOperation in experiment
6.0 g at 0 - 20℃; for 3 h; Inert atmosphere In a 250-mL round-bottomed flask, a solution of 3-methylpyridin-2-amine (4.57 g, 42.3 mmol) in AcOH (50 mL) was cooled to 0 °C. NIS (9.5 g, 42 mmol, Sigma- Aldrich, India) was added in portions to the above solution at the same temperature under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred at room temperature for 3 h. The reaction mixture was diluted with cold water (100 mL), followed by a mixture of 5percent Na2S203 (40 mL) and NaHC03 (100 mL) at room temperature. The solid that formed was filtered, washed thoroughly with water and dried rigorously under reduced pressure at 50 °C to give 5-iodo-3-methyl-2-pyridinamine (6.0 g) as a yellow solid.
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 16, p. 5356 - 5359
[2] Bioorganic Chemistry, 2001, vol. 29, # 4, p. 198 - 210
[3] Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6512 - 6513
[4] Patent: WO2013/123444, 2013, A1, . Location in patent: Page/Page column 213
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  • [ 289681-47-6 ]
Reference: [1] Bioorganic Chemistry, 2001, vol. 29, # 4, p. 198 - 210
[2] Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6512 - 6513
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