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Chemical Structure| 203450-08-2
Chemical Structure| 203450-08-2
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Product Details of [ 203450-08-2 ]

CAS No. :203450-08-2 MDL No. :MFCD28964710
Formula : C21H14FN3 Boiling Point : -
Linear Structure Formula :- InChI Key :DEFTZOFCLNDIMR-UHFFFAOYSA-N
M.W : 327.35 Pubchem ID :15850059
Synonyms :

Calculated chemistry of [ 203450-08-2 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 96.09
TPSA : 38.67 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.9
Log Po/w (XLOGP3) : 5.06
Log Po/w (WLOGP) : 5.43
Log Po/w (MLOGP) : 4.35
Log Po/w (SILICOS-IT) : 5.36
Consensus Log Po/w : 4.82

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.57
Solubility : 0.000881 mg/ml ; 0.00000269 mol/l
Class : Moderately soluble
Log S (Ali) : -5.61
Solubility : 0.000796 mg/ml ; 0.00000243 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -9.09
Solubility : 0.000000269 mg/ml ; 0.0000000008 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 203450-08-2 ]

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

Application In Synthesis of [ 203450-08-2 ]

* 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.

  • Downstream synthetic route of [ 203450-08-2 ]

[ 203450-08-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 6558-83-4 ]
  • 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
  • 9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,8-dimethyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% Stage #1: 1,8-dimethyl-9H-carbazole With sodium hydride In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux; 4.2.1. 9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,8-dimethyl-9H-carbazole (DmCzTrz) 1,8-dimethyl-9H-carbazole (0.39 g, 2.02 mmol) in N,N-dimethylformamide(20 ml) was slowly added into a flask containingsodium hydride (0.09 g, 3.67 mmol) and stirred for 30 min under anitrogen atmosphere. Then, 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (0.60 g, 3.67 mmol) was added above flask and refluxed for24 h. Reaction mixture was cooled down to room temperature andwashed with ethyl acetate and distilled water. The residue wasrecrystallized in toluene. After vacuum train sublimation, 0.38 g ofthe title product was obtained white powder.Yield: 0.38 g, 41%. MS(APCI) 502 m/z. 1H NMR (500 MHz, CDCl3): δ 1.19 (s, 6H), 7.12 (d, 2H, J 7.50 Hz), 7.18 (t, 2H, J 7.50 Hz),7.58-7.63 (m, 6H), 7.72 (d, 2H, J 8.50 Hz), 8.02 (d, 2H, J 7.50 Hz),8.81 (d, 4H, J 9.50 Hz), 8.91 (d, 2H, J 8.50 Hz). Elemental analysiscalcd for C35H26N4: C, 83.64; H, 5.21; N, 11.15. Found: C, 84.03; H,4.82; N, 10.94.
  • 2
  • [ 6558-85-6 ]
  • 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
  • 9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-1,3,6,8-tetramethyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 1,3,6,8-tetramethyl-9H-carbazole With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 150℃; for 12h; Inert atmosphere;
  • 3
  • [ 3842-55-5 ]
  • [ 1765-93-1 ]
  • 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at -20℃; Reflux;
93% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Inert atmosphere; Reflux; 1 Synthesis of intermediate M1-3: Take a dry 250mL double-necked bottle,3.1 g (22 mmol) of 4-fluorophenylboronic acid,5.3 g (20 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 3.0 g (22 mmol) of anhydrous potassium carbonate, After replacing with nitrogen three times, 288 mg (0.25 mmol) of tetratriphenylphosphine palladium, 11 mL of water and 150 mL of tetrahydrofuran were added. The reaction was heated to reflux under a nitrogen atmosphere for 10 h. After the reaction was stopped, the solvent in the reaction system was distilled off under reduced pressure to obtain a large amount of brown-yellow solid. The crude product was dissolved in 200 mL of dichloromethane. After washing with a large amount of water, the organic phases were combined and dried over anhydrous magnesium sulfate. After concentration, silica gel column chromatography was used for separation. The solution was concentrated to obtain 6.1 g of a white solid with a yield of 93%. The molecular ion mass determined by mass spectrometry is: 327.21 (calculated value: 327.12); theoretical element content (%) C21H14FN3: C, 77.05; H, 4.31; F, 5.80; N, 12.84. Measured element content (%): C, 77.06; H, 4.21; F, 5.85; N, 12.88. The above analysis results show that the obtained product is the expected product M1-3.
93% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 10h; Inert atmosphere; Reflux; 1 Synthesis of intermediate M1-1 Take a dry 250mL double-necked bottle and add 3.1g (22mmol) 4-fluorophenylboronic acid,5.3 g (20 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 3.0 g (22 mmol) of anhydrous potassium carbonate,After replacing with nitrogen three times, 288 mg (0.25 mmol) of tetratriphenylphosphine palladium, 11 mL of water and 150 mL of tetrahydrofuran were added.The reaction was heated to reflux under a nitrogen atmosphere for 10 h.After the reaction was stopped, the solvent in the reaction system was distilled off under reduced pressure to obtain a large amount of brown-yellow solid.The crude product was dissolved in 200 mL of dichloromethane. After washing with a large amount of water, the organic phases were combined and dried over anhydrous magnesium sulfate.After concentration, silica gel column chromatography was used for the separation. Petroleum ether: dichloromethane = 8: 1 was used for elution. The eluent was concentrated to give M1-1 as a white solid, 6.1 g, with a yield of 93 %
90% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 106℃; for 12h; Inert atmosphere;
86% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 60℃; for 8h; Inert atmosphere;
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 4h; Inert atmosphere; Reflux;
82% Stage #1: 2-chloro-4,6-diphenyl-1,3,5-triazine; 4-fluoroboronic acid With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60℃; for 0.00333333h; Inert atmosphere; Sealed tube; Stage #2: With potassium carbonate In tetrahydrofuran; water at 80℃; for 0.24h; Inert atmosphere; Sealed tube; 1.2 (2) Preparation of F-TRZ First prepare a mixed aqueous solution of 10 mL of K2CO3 (2 mol / L) and an organic phase of tetrahydrofuran solution of 30 mL, and bubbling nitrogen continuously for 3 hours. Take out the 250 mL three-necked flask, magnet, and spherical condenser tube and assemble the device. Add 4-fluorophenylboronic acid (5 g, 35.7 mmol), (9.5 g, 35.7 mmol), and tetratriphenylphosphine palladium (1.5 g, 1.78 mmol) to the three-necked bottle in order according to the feed ratio, and seal the device. Vacuum the device 3-4 times (ventilation N2), put the device in an oil bath, and inject the tetrahydrofuran phase system into the reaction flask, and heat and stir at 60 ° C. After about 20 minutes of reaction, 10 mL of an aqueous solution was injected into the system, and the system was allowed to react for about 24 hours under stirring at 80 ° C to stop the reaction. The reaction was quenched by adding water, extracted with dichloromethane, dried over anhydrous Na2SO4, filtered with suction, rotary evaporation, and column chromatography (silica gel 200-300 mesh, eluent V petroleum ether: V dichloromethane = 4: 1) to obtain pure white. Product of F-TRZ (9.6 g, 82%).
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; 2 Preparation of Comparative Intermediate 2-a' 2-chloro-4,6-diphenyl-1,3,5-triazine 20 g (74.7 mmol), (4-fluorophenyl) boronic acid 11.5 g (82.2 mmol), Pd(PPh3)4 4.3 g (3.7 mmol), potassium carbonate 20.6 g (149.4 mmol) was suspended in 380 ml of toluene, 75 ml of ethyl alcohol, and 75 ml of distilled water, followed by reflux agitation for 12 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and then subjected to silica gel column to obtain Comparative Intermediate 2-a', 19.6 g (yield: 80%).
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; 2-1 2-1) Preparation of Comparative Compound 2-1 2-chloro-4,6-diphenyl-1,3,5-triazine 20 g (74.7 mmol), (4-fluorophenyl) boronic acid 11.5 g (82.2 mmol), Pd(PPh3)44.3 g (3.7 mmol) and potassium carbonate 20.6 g (149.4 mmol) were suspended in 380 ml of toluene, 75 ml of ethyl alcohol, and 75 ml of distilled water, followed by reflux stirring for 12 hours.After the reaction was completed, extraction was performed with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and purified by a silica gel column to obtain Comparative Compound 2-1, 19.6 g (yield: 80%).
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; 2.2-1 2-1) Synthesis of Comparative Compound 2-1 2-chloro-4,6-diphenyl-1,3,5-triazine 20 g (74.7 mmol), (4-fluorophenyl) boronic acid 11.5 g (82.2 mmol), Pd(PPh3) 44.3 g ( 3.7 mmol) and potassium carbonate 20.6 g (149.4 mmol) were suspended in 380 ml of toluene, 75 ml of ethyl alcohol, and 75 ml of distilled water, followed by reflux agitation for 12 hours. After the reaction was completed, extraction was performed with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and then subjected to silica gel column to obtain Comparative Compound 2-1, 19.6 g (yield: 80%).
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; 3.3-1 3-1) Preparation of Comparative Compound 3-1 2-chloro-4,6-diphenyl-1,3,5-triazine 20 g (74.7 mmol), (4-fluorophenyl) boronic acid 11.5 g (82.2 mmol), Pd(PPh3)44.3 g (3.7 mmol) and potassium carbonate 20.6 g (149.4 mmol) were suspended in 380 ml of toluene, 75 ml of ethyl alcohol, and 75 ml of distilled water, followed by reflux stirring for 12 hours.After the reaction was completed, extraction was performed with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and then subjected to silica gel column to obtain Comparative Compound 3-1, 19.6 g (yield: 80%).
2.8 g With bis(tri-phenylphosphine)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 110℃; for 12h; Inert atmosphere; 1.3 Synthesis of TRZPhF (4-fluorophenyl) boronic acid (1.4 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.3 g, 8.6 mmol)And bis (triphenylphosphine) palladium dichloride (0.3 g, 0.4 mmol)For a mixture in foamed dioxane (30 mL) consisting ofPotassium carbonate (2.4 g, 17.2 mmol) in bubbled water (10 mL) was added and reacted by heating at 110 ° C. for 12 hours under argon. After cooling to room temperature, the mixture was diluted with chloroform,Washed with water. Combine the organic extracts,Dried over magnesium sulfate and concentrated in vacuo.Dilute the crude product with dichloromethane,Filter through a silica gel plug,TRZPhF was obtained as a white solid(Yield 2.8 g).
20.3 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere; 1 Synthesis of P1 In a nitrogen atmosphere, 2-chloro-4,6-diphenyl-1,3,5-triazine (20.00g, 74.7mmol), 4-fluorophenylboronic acid (10.45g, 74.7mmol),Tetrakis(triphenylphosphine)palladium (1.72g, 1.5mmol), potassium carbonate (20.62g, 149.4mmol), 300ml of dioxane, 100ml of distilled water were put into a 1L reaction vessel, and the reaction was refluxed at 100°C for 12h. Cool to room temperature, combine and concentrate the organic phases. It was separated by column chromatography to obtain 20.3 g of intermediate M1.

Reference: [1]Kang, Yu Jin; Yun, Ju Hui; Han, Si Hyun; Lee, Jun Yeob [Journal of Materials Chemistry C, 2019, vol. 7, # 15, p. 4573 - 4580]
[2]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN110396081, 2019, A Location in patent: Paragraph 0069; 0070; 0073; 0074
[3]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN110386923, 2019, A Location in patent: Paragraph 0062; 0063; 0067
[4]Li, Yun; Liang, Jiao-Jiao; Li, Hong-Cheng; Cui, Lin-Song; Fung, Man-Keung; Barlow, Stephen; Marder, Seth R.; Adachi, Chihaya; Jiang, Zuo-Quan; Liao, Liang-Sheng [Journal of Materials Chemistry C, 2018, vol. 6, # 20, p. 5536 - 5541]
[5]Cui, Lin-Song; Nomura, Hiroko; Geng, Yan; Kim, Jong U.k.; Nakanotani, Hajime; Adachi, Chihaya [Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1571 - 1575][Angew. Chem., 2017, vol. 129, # 6, p. 1593 - 1597]
[6]Lee, Kyung Hyung; Jeon, Soon Ok; Chung, Yeon Sook; Numata, Masaki; Lee, Hasup; Lee, Eun Kyung; Kwon, Eun Suk; Sim, Myungsun; Choi, Hyeonho; Lee, Jun Yeob [Journal of Materials Chemistry C, 2020, vol. 8, # 5, p. 1736 - 1745]
[7]Current Patent Assignee: NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS - CN110437211, 2019, A Location in patent: Paragraph 0021-0022; 0024
[8]Current Patent Assignee: SOULBRAIN CO.,LTD. - KR2020/78254, 2020, A Location in patent: Paragraph 0177-0180
[9]Current Patent Assignee: SOULBRAIN CO.,LTD. - KR2021/9942, 2021, A Location in patent: Paragraph 0183-0185
[10]Current Patent Assignee: SOULBRAIN CO.,LTD. - KR2021/33332, 2021, A Location in patent: Paragraph 0183-0186
[11]Current Patent Assignee: SOULBRAIN CO.,LTD. - KR2021/24923, 2021, A Location in patent: Paragraph 0202; 0203-0205
[12]Current Patent Assignee: KYUSHU UNIVERSITY - JP2019/206511, 2019, A Location in patent: Paragraph 0081; 0086-0087
[13]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN112110896, 2020, A Location in patent: Paragraph 0076-0079
  • 4
  • [ 203450-08-2 ]
  • [ 1381986-21-5 ]
  • [ 2093199-14-3 ]
YieldReaction ConditionsOperation in experiment
30.3% Stage #1: 5,13-dihydro-5,5-dimethylbenzofuran[3,2-c]acridine With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide for 7h; Reflux;
Stage #1: 5,13-dihydro-5,5-dimethylbenzofuran[3,2-c]acridine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide for 5h; Reflux; 4 Based on the reaction expression 4, a fourth compound is synthesized which has a molecular structure expressed as a chemical formula of a product in the reaction expression 4 (corresponding to the above chemical formula9). Specifically, sodium hydride (0.30 g, 12.21 mmol) is washed using hexane and then is vacuum-dried. A small amount of dimethylformamide is added to the dried sodium hydride to form a first mixture. Acridine furan derivative solution (1.00 g, 136 mmol) dissolved in 20 ml dimethylformamide is added dropwise slowly to the first mixture, to form a second mixture which, in turn, is kept for 30 minutes at a room temperature. Then, 2-(4-fluorophenyl)4,6-diphenyl-1,3,5-triazine solution (1.00 g, 3.05 mmol) is added dropwise slowly to the second mixture to form a third mixture. In this connection, when 2-(4-fluorophenyl)4,6-diphenyl-1,3,5-triazine is not completely dissolved in dimethylformamide, the third mixture is refluxed using a heat applied thereto. After 5 hours, water is added to the refluxed solution to terminate the reaction. A target product is extracted using distilled water and methylene chloride. Then, the target product is subjected to the polar column chromatography using a mixture solvent of methylene chloride and n-nucleic acid, to acquire a yellow powder 0.4 g. Then, the yellow powder is subjected to purification by sublimation as a dry purification to acquire the fourth compound 0.2 g. The final product has a mass analysis (ASAP) m/z 606.71 [(M)+] 1H NMR (400 MHZ, DMSO): δ: 8.27-8.25 (d, 2H, J=3.80 Hz), 8.11-8.10 (d, 1H, J=1.00 Hz), 7.95-7.93 (t, 1H, J=4.00 HZ), 7.78-7.76 (m, 4H), 7.66-7.59 (m, 2H), 7.54-7.50 (m, 2H), 7.41-7.35 (m, 6H), 7.32-7.23 (m, 2H), 7.18-7.14 (t, 4H, J=4.00 HZ), 6.93-6.89 (t, 3H, J=5.33 Hz), 6.47-6.45 (d, 3H, J=4.00 Hz) 13C NMR (100 MHZ, CDCl3): δ 172.21, 170.25, 156.86, 143.03, 140.27, 133.55, 134.11, 132.80, 131.14, 130.23, 128.18, 126.26, 124.73, 122.25, 120.12, 113.20, 104.72.
  • 5
  • [ 16807-11-7 ]
  • 2-di(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
  • C33H21BrN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With caesium carbonate In N,N-dimethyl-formamide at 190℃; for 16h; 2 Preparation of Comparative Intermediate 2-b' Comparative intermediate 2-a' 19.6 g (59.9 mmol), 1-bromo-9H-carbazole 14.7 g (59.9 mmol), cesium carbonate 39.0 g (119.7 mmol) were suspended in 300 ml of dimethylformamide for 16 hours. It was stirred at 190°C. After the reaction was completed, extraction was performed with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and then subjected to silica gel column to obtain Comparative Intermediate 2-b', 24.9 g (yield: 75%).
  • 6
  • [ 25069-86-7 ]
  • 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
  • C39H28N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.9% Stage #1: 4-hydroxytriphenylamine With potassium carbonate; toluene In 1-methyl-pyrrolidin-2-one at 140℃; for 2h; Inert atmosphere; Stage #2: 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In 1-methyl-pyrrolidin-2-one at 190℃; Inert atmosphere; 1 M9 (0.9 g, 3.45 mmol) and potassium carbonate (0.32 g, 4.5 mmol) were added to a three-necked reaction flask, and under argon protection, 5 mL of N-methylpyrrolidone and 5 mL of toluene were added. At 140°C, reflux with a condenser connected to a water separator. After 2 h, the reaction was cooled to room temperature. 5 mL of M2 (0.98 g, 3 mmol) dissolved in N-methylpyrrolidone was added, the temperature was raised to 190° C., and the reaction was detected by thin layer chromatography. After the reaction, the filtrate was washed with deionized water, the organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated. Silica gel column chromatography, eluted with a mixed solvent of petroleum ether: dichloromethane 10:1, to obtain 0.5 g of a white solid with a yield of 76.9%.
  • 7
  • [ 6962-04-5 ]
  • [ 203450-08-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
80 % Stage #1: bis(4-chlorophenyl)amine With sodium hydride In N,N-dimethyl acetamide at 0 - 20℃; Inert atmosphere; Stage #2: 2-(4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl acetamide at 0 - 100℃; Inert atmosphere;
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