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[ CAS No. 943026-40-2 ] {[proInfo.proName]}

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Chemical Structure| 943026-40-2
Chemical Structure| 943026-40-2
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Product Details of [ 943026-40-2 ]

CAS No. :943026-40-2 MDL No. :MFCD09907908
Formula : C6H5ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PVPVPUGHBYWWMK-UHFFFAOYSA-N
M.W : 172.57 Pubchem ID :55267440
Synonyms :

Safety of [ 943026-40-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 943026-40-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 943026-40-2 ]

[ 943026-40-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 17284-80-9 ]
  • [ 943026-40-2 ]
YieldReaction ConditionsOperation in experiment
77% With lithium hydride In 1,4-dioxane at 20℃; for 1 h; (c) 3-Chloro-6,7-dihydro[1,4]dioxino[2,3-c]pyridazineA solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo-derivative (15.46 g; 0.0703 mol) in dry dioxan (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110° C. overnight. The reaction mixture was quenched with wet dioxan, then iced-water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5.x. with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca. 77percent) (containing ca. 15percent of a bromo species).MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+)
77% With lithium hydride In 1,4-dioxane at 20 - 110℃; (c) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo-derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110 0C overnight. The reaction mixture was quenched with wet 1 ,4-dioxane, then iced-water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5x with chloroform, dried (sodium sulphate) <n="34"/>and evaporated to afford a white solid (12.4 g, ca.77percent) (containing ca. 15percent of a bromo species).MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+)
77% With lithium hydride In 1,4-dioxane at 20 - 110℃; (j) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo- derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110 0C overnight. The reaction mixture was quenched with wet 1,4- dioxane, then iced- water. The solution was evaporated to half volume, taken to pH 8 <n="56"/>with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5x with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca.77percent) (containing ca. 15percent of a bromo species). MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+).
77% With lithium hydride In 1,4-dioxane at 20 - 110℃; (c) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol containing some bromo- derivative (15.46 g; 0.0703 mol) in dry 1,4-dioxane (1.2 L) was treated with lithium hydride (2.3 g; 0.28 mol) in portions and stirred at room temperature for 1 hour under argon, then heated at 110 0C overnight. The reaction mixture was quenched with wet 1,4- dioxane, then iced- water. The solution was evaporated to half volume, taken to pH 8 with 5M hydrochloric acid and evaporated to dryness. Water was added and the residue was extracted 5x with chloroform, dried (sodium sulphate) and evaporated to afford a white solid (12.4 g, ca.77percent) (containing ca. 15percent of a bromo species). MS (+ve ion electrospray) m/z 173/5 (Cl MH+); 217/9 (Br MH+)
55% With sodium hydride In tetrahydrofuran at 80℃; for 72 h; (c) 3-Chloro-6,7-dihydro[l,4]dioxino[2,3-c]pyridazine; A solution of 2-[(3,6-dichloro-4-pyridazinyl)oxy]ethanol (5.5g) in tetrahydrofuran (4.5 litres) was treated with sodium hydride (60percent dispersion in oil, 8g) and heated at 80 deg C for 72 hours. The reaction mixture was quenched with wet tetrahydrofuran then ice and evaporated to dryness. The residue was chromatographed on silica eluting with 0- 100percent ethyl acetate in hexane affording a white solid (2.5g, 55percent) containing some bromo species (5percent). MS (+ve ion electrospray) m/z 173 (MH+).
33% With sodium hydride In 1,4-dioxane at 110℃; for 18 h; To a solution of 2-[(3,6-dichloropyridazin-4-yl)oxy]ethan-1-ol 49a (4.52 g, 21.61 mmol) in 1 , 4-dioxane (250 ml_) was added NaH (60percent, 2.07 g, 86.44 mmol) and the reaction heated to 1 10°C for 18 h. After cooling, the reaction was quenched with iced water, reduced in volume and extracted with DCM (3 x 75 ml_). The combined organic extracts were washed with H2O, dried over MgS04 and concentrated. The crude material was purified by silica gel chromatography eluting with 0-3percent MeOH in EtOAc to give 3-chloro-6H,7H-[1 ,4]dioxino[2,3- c) pyridazine 49b (1.22 g, 33percent). LC-MS (Method A) 173.0 [M+H]+ 1.27 min.

Reference: [1] Patent: US2008/221110, 2008, A1, . Location in patent: Page/Page column 18
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2464 - 2469
[3] Patent: WO2008/128953, 2008, A1, . Location in patent: Page/Page column 32-33
[4] Patent: WO2008/128961, 2008, A1, . Location in patent: Page/Page column 54-55
[5] Patent: WO2008/128942, 2008, A1, . Location in patent: Page/Page column 124
[6] Patent: WO2008/3690, 2008, A1, . Location in patent: Page/Page column 35
[7] Patent: WO2017/137744, 2017, A1, . Location in patent: Page/Page column 153
[8] Patent: WO2007/71936, 2007, A1, . Location in patent: Page/Page column 72
[9] Patent: WO2008/6648, 2008, A1, . Location in patent: Page/Page column 53-54
[10] Patent: US2010/56502, 2010, A1, . Location in patent: Page/Page column 17
[11] Patent: WO2007/115947, 2007, A1, . Location in patent: Page/Page column 31
  • 2
  • [ 1003944-30-6 ]
  • [ 17284-80-9 ]
  • [ 943026-40-2 ]
  • [ 1003944-31-7 ]
Reference: [1] Patent: WO2008/9700, 2008, A1, . Location in patent: Page/Page column 39
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