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[ CAS No. 1556-34-9 ] {[proInfo.proName]}

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Chemical Structure| 1556-34-9
Chemical Structure| 1556-34-9
Structure of 1556-34-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1556-34-9 ]

CAS No. :1556-34-9 MDL No. :MFCD01321146
Formula : C14H10BrN Boiling Point : -
Linear Structure Formula :- InChI Key :MZFYKBHQWLWIBI-UHFFFAOYSA-N
M.W : 272.14 Pubchem ID :150930
Synonyms :

Calculated chemistry of [ 1556-34-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.09
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 4.09
Log Po/w (WLOGP) : 4.13
Log Po/w (MLOGP) : 3.71
Log Po/w (SILICOS-IT) : 4.5
Consensus Log Po/w : 3.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.69
Solubility : 0.00561 mg/ml ; 0.0000206 mol/l
Class : Moderately soluble
Log S (Ali) : -4.07
Solubility : 0.0234 mg/ml ; 0.0000859 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.63
Solubility : 0.0000634 mg/ml ; 0.000000233 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 1556-34-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1556-34-9 ]

* 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 [ 1556-34-9 ]

[ 1556-34-9 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 611-64-3 ]
  • [ 1556-34-9 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; dibenzoyl peroxide In chloroform for 5h; Heating;
95% With N-Bromosuccinimide; dibenzoyl peroxide In 1,1,2,2-tetrachloroethylene at 20 - 60℃; for 5h; Large scale; Further stages; 1-6 Example 6 The preparation method of 9-bromomethyl acridine After mixing (60kg) 9-methylacridine and (300kg) tetrachloroethylene at room temperature, add (38kg) N bromosuccinimide and (3kg) BPO under stirring, and stir for 60min For dispersion, the temperature is raised to 40°C, and the reaction is kept for 1 hour. (2) Then the temperature was increased to 55C and the reaction was incubated for 1h.(3) After that, the temperature was lowered to 25° C., N-bromosuccinimide was added (18.8 kg), and the temperature was raised to 60° C. and the reaction was incubated, TLCCentral control, the reaction is complete in 2h.[0060] (4) Cool down to 25° C. and keep the temperature for 1 h. The solid obtained by filtration is the crude 9-bromomethyl acridine, which is then added to the crude product.Add (240kg) 50% methanol aqueous solution, heat up to 20°C, after keeping it for 3h, decrease the temperature to 25°C, keep it warm and stir for 2h, filter and dryObtained a yellow solid powder of 9-bromomethylacridine (81.2kg, purity 98.9%, yield 95.0%)
87% Stage #1: 9-methyl-acridine With 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 60℃; for 0.5h; Stage #2: With N-Bromosuccinimide In tetrachloromethane at 60 - 80℃; for 4h; 5.2.10 9-(Bromomethyl)acridine (12) To a solution of 11 (2.0g, 10.4mmol) in CCl4 (100mL) was added AIBN (0.17g, 1.0mmol) and heated to 60°C under stirring for 30min. Then NBS (0.17g, 11.4mmol) was added and the reaction mixture was heated under refluxing conditions for 4h. After completion of the reaction, the reaction solution was diluted with CH2Cl2. The organic layer was separated, dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel using petroleum ether/EtOAc (5/1) as eluent to afford intermediate 12 (2.45g) in 87% yield. 1H NMR (400MHz, DMSO-d6) δ 8.85 (d, J=8.8Hz, 1H), 8.29 (d, J=8.6Hz, 4H), 7.98-7.94 (m, 2H), 7.80 (d, J=7.7Hz, 1H), 5.89 (s, 2H). MS (ESI) m/z calcd for C14H10BrN [M+ H]+, 272.0, found: 274.3.
87% Stage #1: 9-methyl-acridine With 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 60℃; for 0.5h; Stage #2: With N-Bromosuccinimide In tetrachloromethane for 4h; Reflux; 7 Example 7: Preparation of 9-(bromomethyl)acridine (9) The intermediate 9-methylacridine (2.0 g, 10.4 mmol) prepared in Example 6 was weighed, 100 mL of carbon tetrachloride was added as a solvent, and the temperature was raised to 60°C. Then, azobisisobutyronitrile (0.17 g, 1.0 mmol) was added as an initiator to the solution, and the mixture was stirred at this temperature for 30 min. Then N-bromosuccinimide (0.17g, 11.4mmol) was added, and the temperature was raised to a reflux state, and heating was continued for 4h. After the completion of the reaction was monitored by TLC, dichloromethane was added to dilute. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product. Then, it was separated by silica gel column chromatography (petroleum ether/ethyl acetate=5:1) to obtain 2.45 g of intermediate 9 with a yield of 87%.
80% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 6h; Irradiation;
77% With N-Bromosuccinimide In dichloromethane 9-(bromomethyl)acridine (10) 9-(bromomethyl)acridine (10) To a solution of 9-methylacridine (1.93 g, 10 mmol) in dichloromethane (100 mL) was added NBS (1.78 g, 10 mmol) portion-wise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1:5) as eluent to afford 10 (2.08 g) in 77% yield. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.8 Hz, 4H), 7.81 (t, J=8.0 Hz, 2H), 7.68 (t, J=8.0 Hz, 2H), 5.42 (s, 2H). 13C NMR (400 MHz, CDCl3) δ 148.9, 138.7, 130.5, 130.1, 126.8, 123.8, 123.4, 23.1. MS (FAB) m/z Calcd for C14H10BrN 272.1. Found 2722. [M]+.
77% With N-Bromosuccinimide In dichloromethane at 20℃; Cooling with ice; [0115] To a solution of 9-methylacridine (1.93 g, 10 mmol) in dichloromethane (100 mE) was added N135 (1.78 g, 10 mmol) portion-wise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1 :5) as eluent to afford 10(2.08 g) in 77% yield. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.8 Hz, 4H), 7.81 (t, J=8.0 Hz, 2H), 7.68 (t, J=8.0 Hz, 2H), 5.42 (s, 2H). 13C NMR (400 MHz, CDCl3)δ148.9,138.7, 130.5, 130.1,126.8,123.8,123.4,23.1. MS (FAI3)mlz Calcd for C,4H,0BrN 272.1. Found 2722. [M]+.
77% With N-Bromosuccinimide In dichloromethane at 20℃; Cooling with ice; 9-Bromomethylacridine (2) To a solution of 9-methylacridine (0.193 g, 1 mmol) in dichloromethane (10 mL) was added N-bromosuccinimide (0.178 g, 1 mmol) portionwise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulphate, and the solvent was removed. The residue was purified by column chromatography (eluent ethyl acetate/petroleum ether = 1/5 v/v). Yield 77%; the % of elementsfound/calculated, C 61.26/61.79, H 3.64/3.70, N 5.03/5.15; 1H NMR (CDCl3), δ, ppm (J, Hz): 5.38 (2H, s); 7.62 (2H, t, J = 7.7); 7.78 (2H, t, J = 7.7); 8.31 (4H, d, J = 8.8).
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Reflux;
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Reflux;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 6h;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 6h;

Reference: [1]Gude, Lourdes; Fernandez, Maria-Jose; Grant, Kathryn B.; Lorente, Antonio [Organic and Biomolecular Chemistry, 2005, vol. 3, # 10, p. 1856 - 1862]
[2]Current Patent Assignee: ZHENGZHOU YUANLI BIOLOGICAL TECH - CN111471014, 2020, A Location in patent: Paragraph 0027-0060
[3]Song, Di; Zhang, Nan; Zhang, Panpan; Zhang, Na; Chen, Weijin; Zhang, Long; Guo, Ting; Gu, Xiaotong; Ma, Shutao [European Journal of Medicinal Chemistry, 2021, vol. 221]
[4]Current Patent Assignee: SHANDONG UNIVERSITY - CN113121439, 2021, A Location in patent: Paragraph 0090-0092
[5]Vilková, Mária; Prokaiová, Marianna; Imrich, Ján [Tetrahedron, 2014, vol. 70, # 4, p. 944 - 961]
[6]Current Patent Assignee: HONG KONG BAPTIST UNIVERSITY - US2012/269738, 2012, A1
[7]Current Patent Assignee: HONG KONG BAPTIST UNIVERSITY - US2016/243264, 2016, A1 Location in patent: Paragraph 0115
[8]Zadykowicz, Beata; Storoniak, Piotr [Journal of Thermal Analysis and Calorimetry, 2017, vol. 129, # 3, p. 1613 - 1624]
[9]Campbell et al. [Journal of the Chemical Society, 1958, p. 1145,1147]
[10]Location in patent: experimental part Bedlcoviova, Zdenka; Imrich, Jn; Kristian, Pavol; Danihel, Ivan; Boehm, Stanislav; Sabolova, Danica; Kozurkova, Maria; Paulikova, Helena; Klika, Karel D. [Heterocycles, 2010, vol. 80, # 2, p. 1047 - 1066]
[11]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[12]Vilková, Mária; Ungvarská Ma̘učká, Lucia; Imrich, Ján [Magnetic Resonance in Chemistry, 2016, vol. 54, # 1, p. 8 - 16]
[13]Bečka, Michal; Vilková, Mária; Salem, Othman; Kašpárková, Jana; Brabec, Viktor; Kožurková, Mária [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017, vol. 180, p. 234 - 241]
  • 2
  • [ 1556-34-9 ]
  • [ 75-50-3 ]
  • [ 62509-60-8 ]
YieldReaction ConditionsOperation in experiment
85% In acetone at 0℃; for 0.5h;
With benzene
  • 4
  • [ 1556-34-9 ]
  • [ 122-52-1 ]
  • [ 22188-24-5 ]
YieldReaction ConditionsOperation in experiment
94% for 4h; Reflux; [0116] The mixture of 10 (1.5 g, 5.5 mmol) and triethyl phosphite (2 mE) was heated to reflux for 4 h. After cooling down to room temperature, the excess triethyl phosphite was removed under vacuum to afford 11(1.7 g) in 94% yield. 1H NMR (400 MHz, CDCl3) δ 8.23 (d, J=8.8 Hz, 2H), 8.17 (d, J=8.8 Hz, 2H), 7.72 (t, J=7.2 Hz, 2H), 7.54 (t, J=7.2 Hz, 2H), 4.13 (d, J=24 Hz, 2H), 3.92-3.77 (m, 4H), 1.04 (t, J=7.2 Hz,6H). 13C NMR (400 MHz, CDCl3) δ 148.4, 148.3, 135.8,135.7, 129.9, 129.8, 125.8, 125.3, 125.2, 124.9, 124.8, 62.4,27.5, 26.1, 16.1.
92% for 4h; Reflux; 5.2.11 Diethyl (acridin-9-ylmethyl)phosphonate (13) The mixture of 12 (1.0g, 3.7mmol) and triethyl phosphite (4mL) was heated to reflux for 4h. After cooling down to room temperature, the excess triethyl phosphite was removed under reduced pressure to afford intermediate 13 (1.1g) in a 92% yield.
92% for 4h; Reflux; 8 Example 8: Preparation of diethyl (acridine-9-methyl)phosphonate (10) Weigh out the intermediate 9-(bromomethyl)acridine (1.0 g, 3.7 mmol) prepared in Example 7 above, and dissolve it in 4 mL of triethyl phosphite, heat the reaction solution to reflux, and react for 4 hours. After the completion of the reaction was monitored by TLC, the reaction solution was cooled to room temperature, and concentrated under reduced pressure to remove excess triethyl phosphite to obtain 1.1 g of an oily substance, namely Intermediate 10, with a yield of 92%.
for 4h; Heating;

  • 5
  • [ 1556-34-9 ]
  • [ 117-10-2 ]
  • 1,8-bis(acridin-9-ylmethoxy)anthracene-9,10-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With sodium hydroxide; tetrabutyl-ammonium chloride In dichloromethane; water at 20℃; for 24h;
  • 6
  • [ 1556-34-9 ]
  • [ 524957-05-9 ]
  • 4'-methyl-[2,2']bipyridinyl-4-carboxylic acid [2-(acridin-9-ylmethyl-methyl-amino)-ethyl]-methyl-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In acetonitrile
  • 7
  • [ 1556-34-9 ]
  • [2,2']bipyridinyl-4,4'-dicarboxylic acid bis-[methyl-(2-methylamino-ethyl)-amide] [ No CAS ]
  • [2,2']bipyridinyl-4,4'-dicarboxylic acid bis-[2-(acridin-9-ylmethyl-methyl-amino)-ethyl]-methyl-amide} [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In acetonitrile
  • 8
  • [ 553-26-4 ]
  • [ 1556-34-9 ]
  • bis-1,1'-[(acridin-9-yl)methyl]-4,4'-bipyridinium dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In acetonitrile at 30℃; for 12h;
  • 9
  • [ 1556-34-9 ]
  • 1-(n-butyl)-4,4'-bipyridinium bromide [ No CAS ]
  • 1-[(acridin-9-yl)methyl]-1'-butyl-4,4'-bipyridinium dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In acetonitrile at 30℃; for 12h;
  • 10
  • [ 553-26-4 ]
  • [ 1556-34-9 ]
  • 9-N-(4,4'-bipyridinium)methylacridine bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% at 120℃; for 0.5h;
  • 11
  • [ 858362-73-9 ]
  • [ 1556-34-9 ]
  • N,N'-bis[2-[(9-acridinylmethyl)methylamino]-ethyl]-N,N'-dimethyl-[1,10-phenanthroline]-2,9-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In acetonitrile at 20℃; for 16h;
  • 12
  • [ 1556-34-9 ]
  • [ 22344-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min
Multi-step reaction with 2 steps 1.1: sodium; 2-nitropropane / methanol; dimethyl sulfoxide / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -10 °C 2.2: 13 h / -10 - 20 °C
Multi-step reaction with 2 steps 1: 4 h / Reflux 2: sodium hydride / mineral oil; tetrahydrofuran / 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1: 4 h / Reflux 2: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C

  • 13
  • [ 1556-34-9 ]
  • [ 88332-45-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min 3: acetone / 12 °C / Irradiation
  • 14
  • [ 1556-34-9 ]
  • [ 88332-47-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min 3: acetone / 12 °C / Irradiation
  • 15
  • [ 1556-34-9 ]
  • [ 88332-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min 3: acetone / 12 °C / Irradiation
  • 16
  • [ 1556-34-9 ]
  • [ 134591-96-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min 3: acetone / 12 °C / Irradiation
  • 17
  • [ 1556-34-9 ]
  • [ 88332-48-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min 3: acetone / 12 °C / Irradiation
  • 18
  • [ 1556-34-9 ]
  • [ 134592-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 4 h / Heating 2: 1.) NaH, 15-crown-5, 2.) EtOH / 1.) THF, 2 h, r. t., 2.) reflux, 30 min 3: 89 percent / SnCl2 / 96 h / Heating 4: acetone / 12 °C / Irradiation
  • 19
  • [ 1556-34-9 ]
  • [ 35426-11-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol 2: water; ethanol; NaOH-solution
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 6 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 6 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 6 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 6 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 6 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 7 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 7 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 8 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 8 h / 20 °C 2: acetonitrile; water / Photolysis
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 9 h / 20 °C 2: acetonitrile; water / Photolysis

Reference: [1]Campbell et al. [Journal of the Chemical Society, 1958, p. 1145,1147]
[2]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[3]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[4]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[5]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[6]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[7]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[8]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[9]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[10]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
[11]Jana, Avijit; Saha, Biswajit; Karthik; Barman, Sharabani; Ikbal, Mohammed; Ghosh, Sudip Kumar; Pradeep Singh [Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 1041 - 1052]
  • 20
  • anhydrons potassium carbonate [ No CAS ]
  • [ 1556-34-9 ]
  • [ 115-69-5 ]
  • 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; ethanol 13 EXAMPLE 13, 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol dihydochoride EXAMPLE 13 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol dihydochoride Bromination of 9-methylacridine (Lancaster Synthesis Ltd., P.O. Box 1000, Industrial Drive, Wyndham, NH 03087) by the procedure of A. Campbell et al , J . Chem . Soc . 1145 (1958) gave 9-bromomethylacridine. To a round bottomed flask equipped with magnetic stirring bar, condenser, and nitrogen inlet tube and bubbler was added 9-bromomethylacridine (10.5g, 38.58 mmol), 2-amino-2-methyl-1,3-propanediol (Aldrich Chemical Co., Milwaukee, WI, 53201, 4.06g, 38.58 mmol), anhydrons potassium carbonate (Mallinckrodt Co., St. Louis, MO, 53147, 10.50g, 76.0 mmol) and abs. ethanol (150 ML). The mixture was refluxed for 4 hours, cooled and filtered. The solvent was then removed by rotary evaporation. The crude product was dissolved in methanol (200 ML) filtered again and diluted to 2L with diethyl ether. The dark coloured crude product wasthen recrystallized one additional time from methanol+/diethyl ether and then twice from methanol to give 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol 0.6H2 mp 210-211°(d), which analyzed correctly for the assigned strucure (C,H,N,Cl).
  • 21
  • [ 4930-98-7 ]
  • [ 1556-34-9 ]
  • [ 908562-82-3 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 60℃; for 24h; 1 In a 40 mL vial, 9-(bromomethyl)acridine (272 mg, 1 mmol) in 10 mL CH3CN (suspension) was added to a solution of 2-(pyridin-2-yl)hydrazine (327 mg, 3 mmol). The reaction mixture was heated and magnetically stirred (60 °C oil bath) for 24 hours. The reaction initially turned clear but soon became cloudy, and remained so throughout the reaction. At the end of the reaction, the mixture was cooled to room EPO temperature and filtered to collect crude product. The crude product was washed with CH2Cl2 and dried, leaving the pure desired product (Calc'd for C19H16N4: 300.1, [M- H]+ found: 299.1).
  • 22
  • [ 1556-34-9 ]
  • [ 827614-44-8 ]
  • [ 908562-75-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine at 40℃; for 8h; 1 To a solution of 9-bromomethylacridine (0.2 g, 0.7 mmo) in 4 mL of DMF was added diisopropylethylamine (0.14 g, 1.1 mmol, 0.2 mL) and 3-isopropyl-1-pheynyl-1H- pyrazol-5-amine (0.18 g, 0.9 mmol). The reaction was stirred at 40 °C for 8 h. Upon cooling, the reaction mixture was partitioned between water and EtOAc. The aqueous layer was washed with EtOAc, and the combined organic extracts were washed with brine and dried over MgSO4. The crude material was purified by silica chromatography (0-40% Hexanes/EtOAc) to afford the desired product. (Calc'd for C26H24N4: 392.5, [M+H]+ found: 393)
  • 23
  • [ 1556-34-9 ]
  • [ 60-29-7 ]
  • [ 115-69-5 ]
  • 2-[(9-Acridinylmethyl)amino]-2methyl-1,3-propanediol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.3% In methanol; ethanol 13 2-[(9-Acridinylmethyl)amino]-2methyl-1,3-propanediol dihydrochloride To a RB flask equipped with magnetic stirring bar, condenser, and N2 inlet line with bubbler was added 9-bromomethylacridine (10.5 g, 39.58 mmol), 2-amino-2-methyl-1,3-propanediol (Aldrich, 4.06 g, 38.58 mmol), anhydrous K2 CO3 (Mallinckrodt, 10.50 g, 76.0 mmol) and abs. EtOH (250 mL). The mixture was refluxed for 4 h, cooled and filtered. The solvent was then removed by rotary evaporation. The crude product was dissolved in CH3 OH (200 mL) filtered again and diluted to 2 L with Et2 O. The dark colored crude product was then recrystallized one additional time from CH3 OH/Et2 O and then twice from CH3 OH to give 3.46 g (24.3% yield) of 2-[(9-acridinylmethyl)amino]-2-methyl-1,3-propanediol dihydrochloride 0.6 H2 O, mp 210°-211° (dec), (C,H,N,Cl).
  • 25
  • [ 1556-34-9 ]
  • [ 22188-24-5 ]
YieldReaction ConditionsOperation in experiment
94% With triethyl phosphite Diethyl acridin-9-ylmethylphosphonate (11) Diethyl acridin-9-ylmethylphosphonate (11) The mixture of 10 (1.5 g, 5.5 mmol) and triethyl phosphite (2 mL) was heated to reflux for 4 h. After cooling down to room temperature, the excess triethyl phosphite was removed under vacuum to afford 11 (1.7 g) in 94% yield. NMR (400 MHz, CDCl3) δ 8.23 (d, J=8.8 Hz, 2H), 8.17 (d, J=8.8 Hz, 2H), 7.72 (t, J=7.2 Hz, 2H), 7.54 (t, J=7.2 Hz, 2H), 4.13 (d, J=24 Hz, 2H), 3.92-3.77 (m, 4H), 1.04 (t, J=7.2 Hz, 6H). 13C NMR (400 MHz, CDCl3) δ 148.4, 148.3, 135.8, 135.7, 129.9, 129.8, 125.8, 125.3, 125.2, 124.9, 124.8, 62.4, 27.5, 26.1, 16.1.
  • 26
  • [ 1556-34-9 ]
  • [ 1403668-31-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethyl phosphite 2: NaH / tetrahydrofuran
Multi-step reaction with 2 steps 1: 4 h / Reflux 2: sodium hydride / tetrahydrofuran / 20 °C
  • 27
  • [ 1556-34-9 ]
  • [ 1403668-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethyl phosphite 2: NaH / tetrahydrofuran 3: acetonitrile
Multi-step reaction with 3 steps 1: 4 h / Reflux 2: sodium hydride / tetrahydrofuran / 20 °C 3: acetonitrile / 24 h / 100 °C
  • 28
  • [ 1556-34-9 ]
  • [ 1403668-18-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethyl phosphite 2: NaH / tetrahydrofuran 3: acetonitrile
Multi-step reaction with 3 steps 1: 4 h / Reflux 2: sodium hydride / tetrahydrofuran / 20 °C 3: acetonitrile / 24 h / 120 °C
  • 29
  • [ 2295-31-0 ]
  • [ 1556-34-9 ]
  • [ 1402724-43-9 ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: thiazoline-2,4-dione With sodium hydroxide In ethanol at 25℃; for 0.166667h; Stage #2: 9-(bromomethyl)acridine In ethanol at 60℃; for 7h;
51% Stage #1: thiazoline-2,4-dione With sodium hydroxide In ethanol at 25℃; for 0.166667h; Stage #2: 9-(bromomethyl)acridine In ethanol at 62℃; for 7h; 2.1.1. Synthesis of 3-(acridin-9-ylmethyl)thiazolidine-2,4-dione (LPSF/AA-1A) (3) Thiazolidine-2,4-dione, compound 3, (1.5 eq) and sodiumhydroxide, previously solubilized in ethanol, were stirred for10 min at room temperature (25°C). 9-Bromomethylacridine,compound 4, (1.0 eq) was added, and the mixture was stirredat 62°C for 7 h. After completion of the reaction, the mixturewas filtered and washed with water. The product obtained wasa yellow solid. Formula: C17H12N2O2S. Melting point (m.p.):196-197°C. Yield: 51%. IR (KBr, cm-1): 2889 (-CH2-), 1750(C=O), 1694 (C=O), 750 (C-H). H1 NMR (300 MHz, DMSOd6)δ 8.42 (d, 2H, J = 8.7 Hz, Acr-H), 8.17 (d, 2H, J = 8.4 Hz,Acr-H), 7.83-7.88 (m, 2H, Acr-H), 7.65-7.70 (m, 2H, Acr-H), 5.75 (s, 2H, N-CH2), 4.23 (s, 2H, S-CH2). MS m/z (%):(M+H) + 309.1 (100), calculated 308; +MS2 309.1 (56), 235(100), 192 (98).
  • 30
  • [ 1556-34-9 ]
  • [ 1402724-49-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 0.17 h / 25 °C 1.2: 7 h / 60 °C 2.1: piperidine / ethanol / 4 h / 50 °C
  • 31
  • [ 1556-34-9 ]
  • [ 1402724-50-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 0.17 h / 25 °C 1.2: 7 h / 60 °C 2.1: piperidine / ethanol / 4 h / 50 °C
  • 32
  • [ 1556-34-9 ]
  • [ 1402724-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 0.17 h / 25 °C 1.2: 7 h / 60 °C 2.1: piperidine / ethanol / 4 h / 50 °C
  • 33
  • [ 1556-34-9 ]
  • [ 1402724-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 0.17 h / 25 °C 1.2: 7 h / 60 °C 2.1: piperidine / ethanol / 4 h / 50 °C
  • 34
  • [ 1556-34-9 ]
  • [ 1402724-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 0.17 h / 25 °C 1.2: 7 h / 60 °C 2.1: piperidine / ethanol / 4 h / 50 °C
  • 35
  • [ 1556-34-9 ]
  • [ 1402724-48-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol / 0.17 h / 25 °C 1.2: 7 h / 60 °C 2.1: piperidine / ethanol / 4 h / 50 °C
  • 36
  • [ 4530-20-5 ]
  • [ 1556-34-9 ]
  • [ 1473417-55-8 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In dichloromethane at 20℃; for 6h;
69% With potassium fluoride In N,N-dimethyl-formamide at 20℃;
  • 37
  • [ 1556-34-9 ]
  • [ 57294-38-9 ]
  • [ 1473417-59-2 ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate In dichloromethane at 20℃; for 6h;
49% With potassium fluoride In N,N-dimethyl-formamide at 20℃;
  • 38
  • [ 1556-34-9 ]
  • [ 15761-38-3 ]
  • [ 1473417-56-9 ]
YieldReaction ConditionsOperation in experiment
93% With potassium fluoride In N,N-dimethyl-formamide at 20℃;
87% With potassium carbonate In dichloromethane at 20℃; for 8h;
  • 39
  • [ 1556-34-9 ]
  • [ 13734-34-4 ]
  • (S)-acridin-9-ylmethyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In dichloromethane at 20℃; for 6h;
  • 40
  • [ 1556-34-9 ]
  • [ 2198-64-3 ]
  • (S)-acridin-9-ylmethyl 2-benzamido-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In dichloromethane at 20℃; for 7h;
  • 41
  • [ 1556-34-9 ]
  • [ 64-19-7 ]
  • [ 101273-70-5 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In dichloromethane at 20℃; for 8h;
  • 42
  • [ 122-39-4 ]
  • [ 1556-34-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc(II) chloride / 5 h / 180 - 220 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux
Multi-step reaction with 2 steps 1: zinc(II) chloride / 6 h / 220 °C 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 6 h / 80 °C / Irradiation
Multi-step reaction with 2 steps 1: zinc(II) chloride / 17 h / 220 °C 2: N-Bromosuccinimide / dichloromethane / 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1.1: zinc(II) chloride / 180 - 200 °C 2.1: 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / 60 °C 2.2: 4 h / 60 - 80 °C
Multi-step reaction with 2 steps 1.1: zinc(II) chloride / 5 h / 180 - 220 °C 2.1: 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / 60 °C 2.2: 4 h / Reflux

  • 43
  • [ 86-87-3 ]
  • [ 1556-34-9 ]
  • (acridin-9-yl)methyl 2-(naphthalene-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In dichloromethane at 20℃; for 8h;
  • 44
  • [ 1556-34-9 ]
  • [ 65-85-0 ]
  • (acridin-9-yl)methyl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In dichloromethane at 20℃; for 9h;
  • 45
  • [ 1556-34-9 ]
  • [ 100-09-4 ]
  • (acridin-9-yl)methyl 4-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate In dichloromethane at 20℃; for 6h;
  • 46
  • [ 1556-34-9 ]
  • [ 55744-85-9 ]
  • (acridin-9-yl)methyl 4-ethoxy-2-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In dichloromethane at 20℃; for 7h;
  • 47
  • [ 1556-34-9 ]
  • [ 74-11-3 ]
  • (acridin-9-yl)methyl 4-chlorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In dichloromethane at 20℃; for 6h;
  • 48
  • [ 1556-34-9 ]
  • [ 7803-57-8 ]
  • [ 132161-56-9 ]
YieldReaction ConditionsOperation in experiment
89% In 1,4-dioxane; ethanol at 0 - 20℃; for 1h; Inert atmosphere;
  • 49
  • [ 1556-34-9 ]
  • [ 30034-22-1 ]
  • [ 1529770-75-9 ]
YieldReaction ConditionsOperation in experiment
32% With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 30h; 4.2.3 N-(2-Nitrobenzyloxycarbonyl)-l-alanine (acridin-9-yl)methyl ester, 6 To a solution of compound 2 (0.073g, 2.73×10-4mol) in dry DMF (3mL), potassium fluoride (0.047g, 8.16×10-4mol) and 9-(bromomethyl)acridine 3 (0.074g, 2.72×10-4mol) were added. The reaction mixture was stirred at room temperature for 30h. Potassium fluoride was removed by filtration, the solvent was removed by rotary evaporation under reduced pressure and the crude residue was purified by column chromatography using mixtures of ethyl acetate and light petroleum of increasing polarity as eluent. Compound 6 was obtained as light brown oil (0.040g, 32%). Rf=0.51 (ethyl acetate/light petroleum, 1:1). 1H NMR (CDCl3, 400MHz): δ=1.33 (d, J 7.2Hz, 3H, β-CH3), 4.30-4.40 (m, 1H, α-CH), 5.45 (s, 2H, CH2 NB), 5.58 (d, J 7.6Hz, 1H, NH), 6.08 (d, J 6.8Hz, 1H, CH2 OAcm), 6.20 (d, J 6.8Hz, 1H, CH2 OAcm), 7.35-7.45 (m, 1H, H-4′), 7.46-7.55 (m, 2H, H-5′and H-6′), 7.56-7.62 (m, 2H, H-2 and H-7), 7.73-7.79 (m, 2H, H-3 and H-6), 8.043 (dd, J 6.4 and 1.6Hz, 1H, H-3′), 8.20-8.30 (m, 4H, H-1, H-8, H-4 and H-5). 13C NMR (CDCl3, 100.6MHz): δ=18.14 (β-CH3), 49.77 (α-CH), 58.57 (CH2 OAcm), 63.37 (CH2 NB), 123.74 (C-1 and C-8), 124.83 (C-3′), 125.16 (C-8a and C-9a), 126.82 (C-2 and C-7), 128.34 (C-4′), 128.41 (C-5′), 129.85 (C-4 and C-5), 130.11 (C-3 and C-6), 132.78 (C-1′), 133.65 (C-6′), 136.49 (C-9), 147.06 (C-2′), 148.32 (C-4a and C-10a), 155.04 (C=O carbamate), 172.69 (C=O ester). IR (film, cm-1): ν=3420, 3331, 3056, 2985, 2941, 2878, 1727, 1630, 1611, 1579, 1526, 1452, 1421, 1344, 1305, 1266, 1209, 1170, 1115, 1068, 966, 910, 897, 859, 819, 790, 738, 704, 674, 642. HRMS (EI): calcd for C25H21N3O6 [M+]: 459.14313; found: 459.14292.
  • 50
  • [ 107-10-8 ]
  • [ 1556-34-9 ]
  • [ 1556-35-0 ]
YieldReaction ConditionsOperation in experiment
70% In diethyl ether at 20℃; for 30h;
  • 51
  • [ 1556-34-9 ]
  • [ 1537222-33-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 40 h / 20 °C
  • 52
  • [ 1556-34-9 ]
  • [ 1160258-78-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 27 h / 20 °C
  • 53
  • [ 1556-34-9 ]
  • 1-(acridine-9-yl)methanamine dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With hexamethylenetetramine In chloroform at 20℃; for 24h;
  • 54
  • [ 1556-34-9 ]
  • C16H17N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C
  • 55
  • [ 1556-34-9 ]
  • C21H19N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C
  • 56
  • [ 1556-34-9 ]
  • C22H21N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C
  • 57
  • [ 1556-34-9 ]
  • C21H18BrN3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C
  • 58
  • [ 1556-34-9 ]
  • C21H18N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C
  • 59
  • [ 1556-34-9 ]
  • C18H19N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C
  • 60
  • [ 1556-34-9 ]
  • [ 1537222-34-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 20 °C
  • 61
  • [ 1556-34-9 ]
  • [ 1160258-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 20 °C
  • 62
  • [ 1556-34-9 ]
  • [ 1537222-35-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 20 °C
  • 63
  • [ 1556-34-9 ]
  • [ 1537222-36-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 50 h / 20 °C 4.1: mesitylenecarbonitrile oxide / tetrahydrofuran / 6 h / 20 °C
  • 64
  • [ 1556-34-9 ]
  • [ 1537222-41-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 20 °C 4.1: mesitylenecarbonitrile oxide / tetrahydrofuran / 6 h / 20 °C
  • 65
  • [ 1556-34-9 ]
  • 4-(acridin-9‴-yl)-3-(n-propyl)-spiro[dihydroacridine-9'(10'H),5-imidazolidine]-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 6 h / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 66
  • [ 1556-34-9 ]
  • [ 1537222-58-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 6 h / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 67
  • [ 1556-34-9 ]
  • [ 1537222-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 6 h / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 68
  • [ 1556-34-9 ]
  • [ 1537222-60-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 6 h / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 69
  • [ 1556-34-9 ]
  • [ 1537222-61-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 6 h / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 70
  • [ 1556-34-9 ]
  • [ 1537222-62-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 6 h / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 71
  • [ 1556-34-9 ]
  • 4-(acridin-9‴-yl)-3-benzyl-spiro[dihydroacridine-9'(10'H),5-imidazolidine]-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 72
  • [ 1556-34-9 ]
  • [ 1537222-64-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 73
  • [ 1556-34-9 ]
  • [ 1537222-65-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 74
  • [ 1556-34-9 ]
  • [ 1537222-66-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 75
  • [ 1556-34-9 ]
  • [ 1537222-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 76
  • [ 1556-34-9 ]
  • [ 1160258-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hexamethylenetetramine / chloroform / 24 h / 20 °C 2.1: sodium carbonate / water 2.2: 20 °C 3.1: benzene / 50 h / 20 °C
  • 77
  • [ 1556-34-9 ]
  • [ 1537222-68-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 30 h / 20 °C 2: chloroform / 20 °C 3: mesitylenecarbonitrile oxide / acetonitrile / 6 h / 20 °C
  • 78
  • [ 1556-34-9 ]
  • [ 100-46-9 ]
  • [ 1556-40-7 ]
YieldReaction ConditionsOperation in experiment
56% In diethyl ether at 20℃; for 30h;
  • 79
  • [ 1556-34-9 ]
  • [ 2419-94-5 ]
  • Boc-Glu-OAcm [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With potassium fluoride In N,N-dimethyl-formamide at 20℃;
  • 80
  • [ 1556-34-9 ]
  • [ 3303-84-2 ]
  • Boc-β-Ala-OAcm [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium fluoride In N,N-dimethyl-formamide at 20℃;
  • 81
  • [ 1556-34-9 ]
  • [ 107-92-6 ]
  • (acridin-9-yl)methyl butyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 15h; Synthesis of (acridin-9-yl)methyl butyrate, 8 To a solution of 9-(bromomethyl) acridine 2 (0.038 g,1.39 x 10-4 mol) in dry DMF (3 mL) potassium fluoride (0.073 g,4.17 x 10-4 mol) and butyric acid (0.014 mL, 1.52 x 10-4 mol) were added. The reaction was followed by TLC (ethyl acetate/light petroleum, 1:1), and stirred at room temperature for 15 h. The solvent was removed by rotary evaporation under reduced pressure and the crude residue was purified by column chromatography using ethyl acetate/light petroleum, mixtures of increasing polarity as eluent. Compound 8 was obtained as a brown oily solid (0.027 g, 69%). Rf = 0.48 (ethyl acetate/light petroleum, 1:1). 1H NMR (400 MHz, CDCl3): δH = 0.89 (t, J = 7.2 Hz, 3H, CH3-CH2-CH2),1.63 (sext, J = 7.2 Hz, 2H, CH3-CH2-CH2), 2.32 (t, J = 7.2 Hz, 2H,CH3-CH2-CH2), 6.12 (s, 2H, CH2), 7.62 (dt, J = 7.6 and 1.2 Hz, 2H,H-2 and H-7), 7.79 (dt, J = 7.8 and 1.2 Hz, 2H, H-3 and H-6), 8.28 (d,J = 8.6 Hz, 2H, H-4 and H-5), 8.34 (d, J = 9.0 Hz, 2H, H-1 and H-8).13C NMR (100.6 MHz, CDCl3): δC = 13.54 (CH3-CH2-CH2), 18.34(CH3-CH2-CH2), 35.96 (CH3-CH2-CH2), 57.31 (CH2), 124.03(C-1 and C-8), 125.32 (C-8a and C-9a), 126.68 (C-2 and C-7),129.97 (C-4 and C-5), 130.08 (C-3 and C-6), 137.53 (C-9), 148.46(C-4a and C-4b), 173.42 (CO). IR (KBr 1%): ν = 3067, 2965, 2934,2875, 1737, 1692, 1629, 1603, 1557, 1519, 1498, 1461, 1441, 1416,1382, 1352, 1303, 1286, 1249, 1165, 1100, 1058, 1040, 1018, 976, 911,862, 753, 733, 643 cm-1. HRMS(ESI) for C18H18NO2 [M+ + H]: calculated 280.13384, found: 280.13403.
  • 82
  • [ 1556-34-9 ]
  • [ 1093980-89-2 ]
YieldReaction ConditionsOperation in experiment
With sodium azide In N,N-dimethyl-formamide at 4℃; for 22h;
  • 83
  • [ 1556-34-9 ]
  • C44H39N7O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 22 h / 4 °C 2: 2,6-dimethylpyridine; copper(I) bromide / tetrahydrofuran / Inert atmosphere 3: copper(I) bromide; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine / tetrahydrofuran; dimethyl sulfoxide; water / 16 h / 20 °C
  • 84
  • [ 1556-34-9 ]
  • C43H33N7O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 22 h / 4 °C 2: 2,6-dimethylpyridine; copper(I) bromide / tetrahydrofuran / Inert atmosphere 3: copper(I) bromide; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine / tetrahydrofuran; dimethyl sulfoxide; water / 16 h / 20 °C
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