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CAS No. : | 1169964-41-3 | MDL No. : | MFCD27965501 |
Formula : | C24H18Br3N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IOJQCIAKNZPJAN-UHFFFAOYSA-N |
M.W : | 588.13 | Pubchem ID : | 102166633 |
Synonyms : |
|
Num. heavy atoms : | 30 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 134.64 |
TPSA : | 38.67 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.18 cm/s |
Log Po/w (iLOGP) : | 5.03 |
Log Po/w (XLOGP3) : | 6.63 |
Log Po/w (WLOGP) : | 7.1 |
Log Po/w (MLOGP) : | 5.53 |
Log Po/w (SILICOS-IT) : | 8.1 |
Consensus Log Po/w : | 6.48 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -7.86 |
Solubility : | 0.00000813 mg/ml ; 0.0000000138 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -7.24 |
Solubility : | 0.0000336 mg/ml ; 0.0000000571 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -12.31 |
Solubility : | 0.0000000003 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.92 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 | UN#: | 3261 |
Hazard Statements: | H315-H318-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | for 5h; Reflux; | |
82% | for 5h; Reflux; | |
80% | for 5h; Inert atmosphere; Reflux; |
5.3 g | for 9h; Reflux; | |
5.3 g | for 9h; Reflux; | |
2 g | In chlorobenzene for 9h; Reflux; | hexamethyl(((1,3,5-triazine-2,4,6-triyl)tris(benzene-4,1-3diyl))tris(methylene))tris(phosphonate) (2). In a 100 mL round-bottom flask, 2,4,6- Tri(p-tolyl)-1,3,5-triazine (3g, 8.5 mmol), NBS (4.5 g, 24 mmol) and BPO (0.3 g, 1.2 mmol) were dissolved into 50 mL chlorobenzene and heated at 110 oC for 7 h. The mixture was filtered and the solvent was removed under vacuum. The resident was dissolved into trimethyl phosphite (10 mL) and refluxed for 9 h. The excessive trimethyl phosphite was removed under vacuum. The residue was purified by column chromatography on silica (dichloromethane:ethanol = 10:1) to afford the product as a white powder (2g, yield: 35%). |
5.3 g | In chlorobenzene for 9h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.5% | With trifluorormethanesulfonic acid at 0 - 20℃; for 13h; Inert atmosphere; | |
96% | With trifluorormethanesulfonic acid at 0 - 20℃; for 20h; Inert atmosphere; | |
96% | With trifluorormethanesulfonic acid at 0 - 20℃; for 24h; Inert atmosphere; |
94% | With trifluorormethanesulfonic acid at 0 - 20℃; for 18h; Inert atmosphere; | 7 Example 7: Preparation of Molecular Scaffold Reagent B (MSR-B) 4-Cyanobenzyl bromide [9] (2.5 g, 12.8 mmol) was added portionwise to trifluoromethanesulphonic acid (3 ml, 33.9 mmol) at 0° C. under N2 and the resultant mixture was stirred at room temperature for 18 h. This was poured onto stirred ice/water mixture and basified with saturated aqueous sodium bicarbonate. The resultant solid was collected by filtration, washed with water and dried under reduced pressure to afford the title compound (MSR-B) as a white solid (2.35 g, 94%). 1H NMR (300 MHz, CDCl3) 4.60 (6H, s), 7.60 (6H, d), 8.75 (6H, d). 13C NMR (75 MHz, CDCl3) 32.7, 129.3, 129.4, 136.1, 142.3, 171.1. LCMS M+H+=589, C24H18Br3N3 requires 588; RT=4.21 mins. |
93% | With trifluoromethylsulfonic anhydride In dichloromethane for 12h; Reflux; | |
91% | With trifluorormethanesulfonic acid at 0 - 20℃; for 24h; | 2.2.1. Synthesis of 2,4,6-tris(4-(bromomethyl)phenyl)-1,3,5-triazine(1A) 4-Bromomethylbenzonitrile (2 g, 10.2 mmol) was added to trifluoromethanesulfonicacid (2.6 mL, 10.2 mmol) in small portionat 0 °C. After addition, the mixture was warmed to room temperatureand stirred for further 24 h, then poured into ice, neutralizedby ammonium hydroxide. The solid phase was collected by filtrationto afford white powder (1.82 g, 91%). m.p. 195 °C. 1H NMR(400 MHz, CDCl3) δ: 8.72 (6H, d, J = 8 Hz), 7.60 (6H, d, J = 8 Hz),4.59 (6H, s). 13C NMR (100 MHz, CDCl3) δ (ppm): 171.5, 142.7,136.5, 129.9, 129.8, 33.1. FTIR (KBr), ν (cm-1): 2922, 2852, 1584,1518, 1415, 1371, 1226, 1178, 1018, 866, 814, 606. ESI MS (m/z):Calcd. For [M+Na]+ 609.81, found 609.80 for [M+Na]+. |
90% | With trifluorormethanesulfonic acid at 0 - 20℃; for 24h; | |
90% | With trifluorormethanesulfonic acid at 0 - 20℃; for 24h; Inert atmosphere; | |
89% | With trifluorormethanesulfonic acid at 0 - 20℃; for 24h; Inert atmosphere; | |
72% | With trifluorormethanesulfonic acid at 0 - 20℃; for 24h; | p-Cyanobenzylbromide 8 (2.50 g,12.8 mmol) was added to trifluoromethanesulfonicacid (3 ml) in small portions at 0 °C. After the addition, the mixture was warmed to roomtemperature and stirred for about 24 hours, and then the reaction mixture was poured into ice,neutralized by ammonium hydroxide. The solid phase was collected by filtration. The whitepowder product was used for the next step without any further purification. (1.80g, 72%). |
72% | With trifluorormethanesulfonic acid In chloroform at 0 - 30℃; for 24h; | |
70% | With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 16h; | |
68% | With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 12h; | |
With trifluorormethanesulfonic acid at 0℃; for 24h; | ||
Acidic conditions; | ||
With trifluorormethanesulfonic acid at -0.16℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In chlorobenzene at 110℃; for 7h; | ||
With N-Bromosuccinimide; dibenzoyl peroxide In chlorobenzene at 110℃; for 7h; | ||
With N-Bromosuccinimide; dibenzoyl peroxide In chlorobenzene at 110℃; for 7h; | hexamethyl(((1,3,5-triazine-2,4,6-triyl)tris(benzene-4,1-3diyl))tris(methylene))tris(phosphonate) (2). In a 100 mL round-bottom flask, 2,4,6- Tri(p-tolyl)-1,3,5-triazine (3g, 8.5 mmol), NBS (4.5 g, 24 mmol) and BPO (0.3 g, 1.2 mmol) were dissolved into 50 mL chlorobenzene and heated at 110 oC for 7 h. The mixture was filtered and the solvent was removed under vacuum. The resident was dissolved into trimethyl phosphite (10 mL) and refluxed for 9 h. The excessive trimethyl phosphite was removed under vacuum. The residue was purified by column chromatography on silica (dichloromethane:ethanol = 10:1) to afford the product as a white powder (2g, yield: 35%). |
With N-Bromosuccinimide; dibenzoyl peroxide In chlorobenzene at 110℃; for 7h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 9 h / Reflux 2: 18-crown-6 ether; potassium <i>tert</i>-butylate / dichloromethane / 4 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 9 h / Reflux 2: 18-crown-6 ether; potassium <i>tert</i>-butylate / dichloromethane / 4 h / 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium azide In N,N-dimethyl-formamide at 20℃; for 12h; | |
42% | With sodium azide In dimethyl sulfoxide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran Reflux; | Synthesis of cinchonine and triazine Based CMPTCs General procedure: mixture of 2, 4, 6-Tris-(4-bromomethyl-phenyl)-[1, 3, 5]triazine 9 (0.1g, 10 mmol),cinchona derivatives 10a or 10b ( 30 mmol) was dissolved in 5 ml of THF and heated toreflux for overnight, the white solid was filtered, washed with diethylether and dried it, to getpure CMPTCs (11a or 11b, 86% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran Reflux; | Synthesis of cinchonine and triazine Based CMPTCs General procedure: mixture of 2, 4, 6-Tris-(4-bromomethyl-phenyl)-[1, 3, 5]triazine 9 (0.1g, 10 mmol),cinchona derivatives 10a or 10b ( 30 mmol) was dissolved in 5 ml of THF and heated toreflux for overnight, the white solid was filtered, washed with diethylether and dried it, to getpure CMPTCs (11a or 11b, 86% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Reflux; Inert atmosphere; | |
92% | at 150℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | at 150℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: methyl 3-[4-(1H-imidazol-1-yl)phenyl]acrylate; 2,4,6-tris(4-(bromomethyl)phen-yl)-1,3,5-triazine In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With ammonium hexafluorophosphate In methanol at 20℃; for 2h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: 1H-imidazole With potassium hydroxide In acetonitrile for 2h; Inert atmosphere; Stage #2: 2,4,6-tris(4-(bromomethyl)phen-yl)-1,3,5-triazine In acetonitrile at 80℃; for 48h; Inert atmosphere; | |
90% | With potassium hydroxide In acetonitrile at 20℃; | 2.2.2. Synthesis of 2,4,6-tris(4-((1H-imidazol-1-yl)methyl)phenyl)-1,3,5-triazine (L1) Imidazole (0.38 g, 5.61 mmol) and potassium hydroxide KOH(0.57 g, 10.2 mmol) were taken in 50 mL round bottom flask, withaddition of 25 mL of acetonitrile and the reaction mixture was stirredfor 2 h at room temperature. Then compound 1A (1 g,1.7 mmol) was added and stirring was continued for further 12 h.Next the solvent was evaporated and washed several times withwater to give desired product as white solid. (0.84 g, 90%). m.p.> 250 °C. δ: 8.72 (6H, d, J = 8 Hz), 7.62 (3H, s), 7.33 (6H, d,J = 8 Hz), 7.14 (3H, s), 6.95 (3H, s), 5.25 (6H, s). 13C NMR(100 MHz, CDCl3)δ (ppm): 171.1, 140.8, 137.5, 136.0, 130.0,129.6, 127.45, 119.3, 50.5. FTIR (KBr), ν (cm-1): 3392, 3106,1584, 1524, 1420, 1368, 1290, 1232, 1178, 1020, 814, 752, 656,600. ESI MS (m/z): Calcd. For [M+H]+ 550.24, found 550.24 for [M+H]+, For [M+Na]+ 572.24, found 572.26 for [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 2,4,6-tris(4-(bromomethyl)phen-yl)-1,3,5-triazine; C13H12N2O In N,N-dimethyl-formamide at 110℃; Schlenk technique; Stage #2: With ammonium hexafluorophosphate In methanol at 20℃; for 2h; | 1 Example 1: Preparation of tridentate imidazolium ligand H3-L1(PF6)3 Under anhydrous and anaerobic operating conditions,2,4,6-tris[4-(bromomethyl)phenyl]-1,3,5-triazine (1 mol),4-imidazole-methyl phenyl acrylate (3 mol),(The ratio of the amount of the two substances is 1:3),DMF solution (20 mL) was placed in a 100 ml Schlenk bottle.Reflow at 110 °C for 12-24 hours,Cool to room temperature,Washed with ethyl acetate,Filtered and drained,The product was placed in a flask dissolved in 150 mL of methanol.Add 4.5 mmol of ammonium hexafluorophosphate,Stir the reaction at room temperature for 2 h,A large amount of white precipitate is produced during the period.Filtered and drained,The product was washed with diethyl ether.Dry in vacuum.Obtained 1.170 g of a colorless solid powder.The yield was 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 4,4'-bipyridine; 2,4,6-tris(4-(bromomethyl)phen-yl)-1,3,5-triazine In N,N-dimethyl-formamide; acetonitrile at 90℃; for 72h; Stage #2: With ammonium hexafluorophosphate In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | Stage #1: 2,4,6-tris(4-(bromomethyl)phen-yl)-1,3,5-triazine; C54H42N9(3+)*3F6P(1-) With tetra-(n-butyl)ammonium iodide In acetonitrile at 80℃; for 72h; Stage #2: With ammonium hexafluorophosphate In methanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | for 18h; Inert atmosphere; Cooling with ice; | Synthetic procedure of 2,4,6-tris[4-(bromomethyl) phenyl]-1,3,5-triazine 2,4,6-Tris[4-(bromomethyl)phenyl]-1,3,5-triazine was synthesized following a previously reported procedure [44]. In a dry 100 ml round bottomfask, 4-bromomethyl-benzonitrile (5 g, 25.5 mmol) was taken and kept it on ice bath. Then triflic acid (5 mL) was added slowly. The mixture was then allowed to stir for 18 h under N2 atmosphere. The resulting yellow mixture was poured into 100 ml of ice cold water and neutralized with concentrated ammonium hydroxide. The white coloured precipitate was filtered off and washed with plenty of water followed by little amount of acetone. The solid compound was dried inan oven at 60 °C to obtained constant weight. Finally 4.3 g (yield: 86%)of pure product were obtained. 1H NMR (CDCl3, 400 MHz): /=8.7 (d,6 H), 7.6 (d, 6 H), 4.6 (s, 6 H) ppm; 13C NMR (CDCl3, 100 MHz): /=33,129, 136, 142, 171 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4,4'-bis-(1H-imidazol-1-yl)biphenyl; 2,4,6-tris(4-(bromomethyl)phen-yl)-1,3,5-triazine In N,N-dimethyl-formamide at 110℃; for 48h; Inert atmosphere; Schlenk technique; Stage #2: With methanol; ammonium tetrafluoroborate Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium bicarbonate In water; acetonitrile at 20℃; | 3 Cyclization Protocol General procedure: The linear peptides and all scaffolds were solved in acetonitrile/water 50/50 at 5 mM concentration. The peptide solutions were further diluted in 1M Ammonium bicarbonate (AMBIC) to final concentration 1 mM. 3 ml 1 mM linear peptide solution was mixed with 1 ml 5 mM scaffold solution (linear peptide/scaffold molar ratio 1/1.6). The reaction mixture was kept at room temperature overnight and the cyclization completion was confirmed by LC-MS (Acquity UPLC CSH C18 column, 1.7 μm, 2.1×30 mm; acetonitrile/water/HCOOH containing buffers and 15 to 600 acetonitrile gradient elution over 10 min). The cyclic peptide was purified using RP-HPLC (Gemini C18-semi prep column, 5 μm, 110 , 250×10 mm; acetonitrile/water/TFA containing buffers and 20 to 80% acetonitrile gradient elution over 20 min). Results of the cyclization protocol are provided in Table 3 below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With tetra-(n-butyl)ammonium iodide In chloroform; acetonitrile for 96h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; acetonitrile for 36h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: thiourea / chloroform; acetone / 16 h / Reflux 1.2: 16 h / 80 °C 2.1: antimony(III) chloride; iodine / benzene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: 2,4,6-tris[4-(bromomethyl)phenyl]-1,3,5-triazine With thiourea In chloroform; acetone for 16h; Reflux; Stage #2: With sodium hydroxide at 80℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pd catalyst |