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[ CAS No. 114703-12-7 ]

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Chemical Structure| 114703-12-7
Chemical Structure| 114703-12-7
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CAS No. :114703-12-7 MDL No. :MFCD09954848
Formula : C8H5BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :241.04 g/mol Pubchem ID :14056380
Synonyms :

Safety of [ 114703-12-7 ]

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

Application In Synthesis of [ 114703-12-7 ]

  • Upstream synthesis route of [ 114703-12-7 ]
  • Downstream synthetic route of [ 114703-12-7 ]

[ 114703-12-7 ] Synthesis Path-Upstream   1~10

  • 1
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YieldReaction ConditionsOperation in experiment
72% at 20℃; for 22 h; Synthesis of 2,4-dichloro-7-morpholin-4-ylquinazoline 87.0 g (1.33 mol) of   sodium cyanate were added to 269.0 g (1.17 mol) of   methyl 2-amino-4-bromobenzoate in 1.2 l of   acetic acid with stirring at room temperature, and the mixture was subsequently stirred for a further 22 h. The reaction mixture was diluted with 1.5 l of   water, and the residue was filtered off with suction. 0.42 l of   sodium hydroxide solution (32percent) was added to the solid, the mixture was diluted with 3.5 l of water and heated on a steam bath for 4 h. After cooling, the solid residue was filtered off with suction. Conventional work-up gave 205.2 g of   7-bromo-1H-benzo[d]-1,3-oxazine-2,4-dione; HPLC/MS (M+H)+=243 as solid.
Reference: [1] Patent: US2013/12489, 2013, A1, . Location in patent: Paragraph 0173
  • 2
  • [ 60-35-5 ]
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YieldReaction ConditionsOperation in experiment
90% at 195℃; for 3 h; Step 4: 7-Bromo-lH-quinazoline-2,4-dioneTo a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195 °C for 3 h. The reaction mixture was allowed to reach 80 °C and water was added. The aqueous reaction mixture was stirred at 80 °C for 5-10 min then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound [10 g, 90percent]. This material was taken to the next step without any further purification.
Reference: [1] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 92
  • 3
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YieldReaction ConditionsOperation in experiment
10 g at 195℃; for 3 h; To a 250 mL round bottom flask, 2-amino-4-bromo-benzoic acid (10 g, 0.0463 mol) and urea (27.78 g, 0.4629 mol) were added. The reaction mixture was stirred at 195° C. for 3 hours. The reaction mixture was allowed to cool to 80° C. and water was added. The aqueous reaction mixture was stirred at 80° C. for 5-10 minutes then allowed to reach room temperature. The solid was filtered, dried and azeotroped with toluene to afford the title compound (10 g, 90percent). This material was taken to the next step without further purification.
Reference: [1] Patent: US2014/38952, 2014, A1, . Location in patent: Page/Page column 0158-0159
  • 4
  • [ 6326-79-0 ]
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Reference: [1] Patent: WO2012/58671, 2012, A1,
[2] Patent: US2014/38952, 2014, A1,
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834
  • 5
  • [ 20776-50-5 ]
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Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834
  • 6
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Reference: [1] Patent: WO2012/58671, 2012, A1,
[2] Patent: US2014/38952, 2014, A1,
  • 7
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Reference: [1] Patent: WO2012/58671, 2012, A1,
[2] Patent: US2014/38952, 2014, A1,
  • 8
  • [ 135484-83-2 ]
  • [ 114703-12-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4904 - 4907
  • 9
  • [ 20776-48-1 ]
  • [ 57-13-6 ]
  • [ 114703-12-7 ]
Reference: [1] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 6,
  • 10
  • [ 114703-12-7 ]
  • [ 959237-68-4 ]
YieldReaction ConditionsOperation in experiment
79% at 20℃; for 36 h; Reflux 205.0 g (0.84 mol) of   7-bromo-1H-benzo[d]-1,3-oxazine-2,4-dione were suspended in 1.26 l (12.59 mol) of   phosphoryl chloride at room temperature, 71.34 ml (0.42 mol) of   N-ethyldiisopropylamine were added, and the mixture was subsequently heated under reflux for 36 h. Conventional work-up gave 193.6 g of   7-bromo-2,4-dichloroquinazoline; HPLC/MS (M+H)+=277/279 as solid
77% for 4 h; Reflux A solution of 26 (1.16 g, 4.81 mmol), POCl3 (4.49 mL, 48.1 mmol) and N,N-Diethylaniline (3.06 mL, 19.25 mmol) was heated at reflux for 4h. After cooling, the mixture was evaporated and the mixture was diluted with H2O and CHCl3. The organic layer was washed with H2O and sat. NaCl, then dried over MgSO4 and filtered. After removal of the solvent in vacuo, the residue was purified by silica gel column chromatography (CHCl3/hexane; 1:1 to 4:1) to give the title compound as slight yellow solid (1.02 g, 77percent). 1H NMR (CDCl3) δ = 7.83 (dd, 1H, J = 1.8, 8.9 Hz), 8.17 (dd, 1H, J = 0.4, 8.9 Hz), 8.20 (dd, 1H, J = 0.4, 1.8 Hz). MS:275.0 (M+)
60% at 130℃; for 12 h; Step 5: 7-Bromo-2, 4-dichloro-quinazolineTo a 250 mL round bottom flask, 7-bromo-lH-quinazoline-2,4-dione (10 g0.0413 mol) was charged. To the same flask POCl3 (100 mL) and DIPEA (6.5 mL, 0.0413 mol) were added. The reaction mixture was maintained at 130 °C for 12 h. The volatiles were evaporated and azeotroped with toluene to get the crude residue. The crude residue was purified using, column chromatography (60-120 silica gel, 10percent> ethyl acetate in hexane) to get the title compound (7 g, 60percent). 1H NMR (300 MHz, CDC13): δ 8.41 (s, 1H), 8.00-8.09 (m, 1H), 7.89-7.91 (m,lH): LC-MS (ESI): Calculated mass: 275.9;Observed mass: 276.8 [M+H]+ (RT: 0.68 min).
7 g With N-ethyl-N,N-diisopropylamine; trichlorophosphate In hexane; ethyl acetate at 130℃; for 12 h; To a 250 mL round bottom flask, 7-bromo-1H-quinazoline-2,4-dione (10 g 0.0413 mol) was added. To the same flask, POCl3 (100 mL) and DIPEA (6.5 mL, 0.0413 mol) were added. The reaction mixture was maintained at 130° C. for 12 hours. The volatiles were evaporated and azeotroped with toluene to provide the crude residue. The crude residue was purified using column chromatography (60-120 silica gel, 10percent ethyl acetate in hexane) to provide the title compound (7 g, 60percent). 1H NMR (300 MHz, CDCl3): δ 8.41 (s, 1H), 8.00-8.09 (m, 1H), 7.89-7.91 (m, 1H): LC-MS (ESI): Calculated mass: 275.9; Observed mass [M+H]+: 276.8. (RT: 0.68 min).

Reference: [1] Patent: US2013/12489, 2013, A1, . Location in patent: Paragraph 0174
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4904 - 4907
[3] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 92-93
[4] Patent: US2014/38952, 2014, A1, . Location in patent: Page/Page column 0160-0161
[5] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 6,
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