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[ CAS No. 763114-25-6 ]

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Chemical Structure| 763114-25-6
Chemical Structure| 763114-25-6
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CAS No. :763114-25-6 MDL No. :MFCD13181869
Formula : C16H8FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :265.24 g/mol Pubchem ID :-
Synonyms :

Safety of [ 763114-25-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 763114-25-6 ]

  • Upstream synthesis route of [ 763114-25-6 ]
  • Downstream synthetic route of [ 763114-25-6 ]

[ 763114-25-6 ] Synthesis Path-Upstream   1~10

  • 1
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YieldReaction ConditionsOperation in experiment
91%
Stage #1: at 8 - 25℃; for 4 h;
Stage #2: With water; sodium hydroxide In acetone at 20 - 90℃; for 1 h;
S3, 10.6 g (40 mmol) of the solid obtained in the step S2 and 80 mL of water were added to the flask, and the mixture was cooled to 8 ° C, and 2.90 mL (60 mmol) of the mass fraction of 80percent hydrazine was added dropwise, and then returned to 25 ° C, and stirring was continued. , react 4h, then join4mL of acetone was stirred for 30min, then added with 13mL of 4mol / L NaOH aqueous solution heated to 90 ° C for 1h, cooled to room temperature, the aqueous phase was extracted with 45mL of methyl tert-butyl ether, and then adjusted to a pH of about 4 with hydrochloric acid, a white solid precipitated , filtered, 40mL cold water floatWashed and recrystallized from ethyl acetate to give 9.7 g of a white solid, yield: 91percent.
91% With hydrazine hydrate; sodium hydroxide In ethanol at 70℃; for 0.166667 h; (3) A solution of sodium hydroxide (0.105 mol) in ethanol (50 mL) and hydrazine hydrate (17 mL) were stirred at a temperature of 70 ° C to obtain a homogeneous mixed solution pumped from the pump E 10 to the third mixing valve 11, pump E11. The flow rate was 2.2 mL/min; and the reaction effluent obtained in the step (2) was 2-fluoro-5-(3-oxo-3H-isobenzofuran-1-ylmethylene)benzonitrile.(0.022 mol) flowed into the third mixing valve at a flow rate of 1.56 mL/min. After thorough mixing, the pump was pumped into a third microreactor in the third continuous microchannel reaction unit for reaction at a reaction temperature of 70 ° C and a residence time of 10 min, the first receiving device 13The reaction effluent was collected, the reaction effluent was cooled to room temperature, and 2 mol/L of dilute hydrochloric acid was added to adjust the pH to 4, stirred for 20 min, and then poured into water (50 mL) and ethyl acetate (50 mL), and the mixture was separated, filtered, washed. And dry to get the anti-tumor drug olapa2-fluoro-5-[(4-oxo-3,4-dihydronaphthyridin-1-yl)methyl]benzoic acid(Compound 3), the yield was 91percent.
77%
Stage #1: at 90℃; for 1 h;
Stage #2: at 70℃; for 18 h;
13N sodium hydroxide solution (50 mL) was added to an aqueous solution (200 mL) containing compound f (37 g, 0.14 mol), and the mixture was heated to 90 ° C for 1 hour. After the reaction was reduced to 70 ° C, hydrazine hydrate (100 mL, 2 mol) was added and the temperature was stirred for 18 hours. The reaction solution was cooled to room temperature and the above system was adjusted to pH = 4 with 8N hydrochloric acid. The filter was washed twice with water (60 mL), twice with diethyl ether (50 mL) and dried in vacuo to give a white solid g: 5 - ((4-oxo-3,4-dihydrazizin-1-yl) methyl) benzoic acid (30.1 g, yield 77percent).
70 g
Stage #1: With sodium hydroxide In water at 20 - 70℃;
Stage #2: With hydrogenchloride; hydrazine hydrate In water at 20 - 70℃;
The above semi dried compound 2-fluoro-5-[(3-oxo-2-benzofuran-1 {3H)- ylidene)methyl] benzonitrile (IV) as obtained by example-1 was suspended in water (500 imL) at room temperature followed by addition of aqueous solution of NaOH (50 g). The resulting reaction mixture was stirred at 60°C to 70 °C. After completion of the hydrolysis, it was cooled to room temperature and acidified by addition of cone. HCI until the pH was changed to 5-6. Then hydrazine hydrate (1 67 g) was added. The resulting reaction mass was stirred at 60°C to 70 °C. The reaction mass was cooled to room temperature, acidified by addition of cone. HCI until the pH was changed 4.0-4.5. The stirring was continued further at room temperature. The obtained precipitate was filtered and washed with water. The crude compound was purified by using isopropanol (or any other polar solvent) to afford pure 2- fluoro-5-[(4-oxo-3,4-di hydrophthalazin-1 -yl)methyl]benzoic acid (V) as a solid (70 g). (Yield: 68percent)

Reference: [1] Patent: CN108558773, 2018, A, . Location in patent: Paragraph 0017; 0021; 0026
[2] Patent: CN108794405, 2018, A, . Location in patent: Paragraph 0036; 0039; 0044; 0058; 0063
[3] Patent: CN106146504, 2016, A, . Location in patent: Paragraph 0136; 0137; 0138; 0151; 0152
[4] Patent: WO2012/71684, 2012, A1, . Location in patent: Page/Page column 23-24
[5] Patent: WO2012/166983, 2012, A1, . Location in patent: Page/Page column 70-71
[6] Patent: US2013/224107, 2013, A1,
[7] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8683 - 8693
[8] Patent: CN106905243, 2017, A, . Location in patent: Paragraph 0064; 0065
[9] Patent: WO2017/191562, 2017, A1, . Location in patent: Page/Page column 15
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  • [ 763111-47-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8683 - 8693
[2] Patent: WO2017/191562, 2017, A1,
  • 3
  • [ 218301-22-5 ]
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YieldReaction ConditionsOperation in experiment
89.5% With triethylamine In dichloromethane at 6 - 20℃; for 4 h; S2, 20 g (82.6 mmol) of the solid obtained in the step S1, 12.3 g (82.6 mmol) of 3-cyano-4-fluorobenzaldehyde and 200 mL of dichloromethane were added to a three-necked bottle, and the mixture was cooled to 6 ° C, and then added dropwise. 9.2 g (91.1 mmol) of triethylamine at room temperature4h, the reaction was monitored by thin layer chromatography, the reaction solution was concentrated to dryness, and the mixture was pulverized with 200 mL of water, filtered, dried, and then pulverized with methyl tert-butyl ether to obtain a white solid 18.4 g, yield 89.5percent, NMR results of the white solid :
Reference: [1] Patent: CN108558773, 2018, A, . Location in patent: Paragraph 0020; 0022; 0025
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YieldReaction ConditionsOperation in experiment
1.2 g With triethylamine In tetrahydrofuran at 15 - 20℃; Preparation of 2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile
To the solution of 2-fluoro-5-formylbenzonitrile (0.74 g, 5 mmol) and dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (1.2 g, 5 mmol) in THF (30 ml) was added triethylamine (0.7 ml, 5 mmol) dropwise at a temperature of below 15° C., which was then slowly rose to ambient temperature and stirred for overnight.
The reaction mixture was concentrated and the residue was added water and stirred for 30 min.
The precipitated solid was collected by filtration, washed with water, hexane, and ether, and dried in vacuo to afford the target compound (1.2 g, 92.3percent) as a light yellow solid (a 50:50 mixture of E and Z isomers), used in next step without further purification.
1HNMR (CDCl3): δ 8.13 (1H, m), 8.05 (1H, m), 7.98 (1H, m), 7.79 (2H, m), 7.61 (1H, m), 7.30 (1H, m), 6.35 (1H, s).
37.2 g With triethylamine In tetrahydrofuran at 15℃; To a solution of sodium methoxide (61.8 g, 1.14 mol) in anhydrous methanol (1 L) was slowly added dimethyl phosphite (97 mL, 1.06 mol) under ice bath. The temperature of the reaction system was kept below 5 ° C and 2-carboxybenzaldehyde (135 g, 0.9 mol) was slowly added dropwise over 20 minutes. The above reaction system gradually rose to room temperature and methanesulfonic acid (81.6 mL, 1.26 mol) was gradually added dropwise over half an hour. After removal of the solvent under reduced pressure, the residue was diluted with water (600 mL) and extracted three times with dichloromethane (500 mL). The organic phases were combined and extracted twice with water (100 mL) and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a pale yellow solid compound 3-oxo-1,3-dihydrobenzofuran-1-yl phosphite, without purification directly into the next step. The compound which has been subjected to the step-down reaction without purification is dissolved 3-oxo-1,3-dihydrobenzofuran-1-yl phosphite (35 g, 0.14 mol) in tetrahydrofuran (330 mL) was added 2-fluoro-5-formylbenzonitrile G, 0.14 mol), system cooling to 15 , triethylamine (19.5 mL, 0.14 mol) was slowly added dropwise over 30 minutes. The above reaction system gradually rose to room temperature, the solvent was removed under reduced pressure, The residue was beaten with water (250 mL) filtration gave a white solid compound f: 2-fluoro-4-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)phenyl cyanide (37.2 g, yield 96percent).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8683 - 8693
[2] Patent: WO2012/71684, 2012, A1, . Location in patent: Page/Page column 23
[3] Patent: WO2012/166983, 2012, A1, . Location in patent: Page/Page column 70
[4] Patent: US2013/224107, 2013, A1, . Location in patent: Paragraph 0141; 0142
[5] Patent: CN106146504, 2016, A, . Location in patent: Paragraph 0136; 0137; 0138; 0149; 0150
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  • [ 17858-15-0 ]
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Reference: [1] Patent: WO2008/47082, 2008, A2, . Location in patent: Page/Page column 27
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  • [ 218301-22-5 ]
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Reference: [1] Patent: WO2017/191562, 2017, A1, . Location in patent: Page/Page column 14; 15
  • 7
  • [ 61260-15-9 ]
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Reference: [1] Patent: CN106905243, 2017, A, . Location in patent: Paragraph 0062; 0063
  • 8
  • [ 119-67-5 ]
  • [ 763114-25-6 ]
Reference: [1] Patent: WO2012/71684, 2012, A1,
[2] Patent: WO2012/166983, 2012, A1,
[3] Patent: US2013/224107, 2013, A1,
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8683 - 8693
[5] Patent: CN106146504, 2016, A,
[6] Patent: CN106905243, 2017, A,
[7] Patent: CN108558773, 2018, A,
  • 9
  • [ 77771-02-9 ]
  • [ 763114-25-6 ]
Reference: [1] Patent: WO2012/71684, 2012, A1,
[2] Patent: US2013/224107, 2013, A1,
  • 10
  • [ 763114-25-6 ]
  • [ 1021298-68-9 ]
Reference: [1] Patent: WO2008/47082, 2008, A2, . Location in patent: Page/Page column 28
[2] Patent: US2013/224107, 2013, A1,
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