Structure of 53760-27-3
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CAS No. : | 53760-27-3 |
Formula : | C12H15N3O4S |
M.W : | 297.33 |
SMILES Code : | NC1=CC=C(NC2=CC=C(N)C=C2)C=C1.O=S(O)(O)=O |
MDL No. : | MFCD00013113 |
InChI Key : | OOZQLPDAELLDNY-UHFFFAOYSA-N |
Pubchem ID : | 104599 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 5.0 |
Molar Refractivity | 79.02 |
TPSA ? Topological Polar Surface Area: Calculated from |
147.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-0.13 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.72 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.04 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.65 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.11 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.45 |
Solubility | 1.06 mg/ml ; 0.00356 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.39 |
Solubility | 0.122 mg/ml ; 0.000411 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.25 |
Solubility | 0.0166 mg/ml ; 0.0000558 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.6 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
1.0 |
Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
1.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.28 |
* 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 |
---|---|---|
With sodium carbonate; In methanol; for 3h;Heating / reflux; | 4,4'-diaminodiphenylamine sulphate 85% (0.5 g, 1.43 mmol) was dissolved in methanol (50 mL) and treated with excess of Na2CO3. The suspension was filtered to remove the Na2CO3 excess and to the solution pyridine-2-carboxaldehyde (0.27 mL, 2.85 mmol) and FeCl2 x 4H2O (0.27 g, 2.85 mmol) were added. The resulting mixture was heated at reflux for 3 hours with a Dean-Stark trap and concentrated to half volume. The addition of diethyl-ether (10 mL) precipitated a solid which was collected by filtration and dried in vacuo. [Fe2(NH2-L)3]Cl4- Yield (0.31 g. 47%); +ve FABMS: m/z = 1313 {Fe2(NH2-L)3CL2}; 1H NMR (DMSO-d6, ppm): d 5.54 (d, 4H, 7.5 Hz), 6.69 (d, 4H, 7,5 Hz), 7.39 (d, 2H, J= 5.6 Hz), 7.60 (dd, 2H, J= 7.5, 5.6 Hz), 8. 20 (t, 2H, 7.8 Hz), 8.43 (d, 2H, 7.5 Hz), 9.07 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In water; for 1h; | 4,4'-diaminodiphenylamine sulphate 85% (0.5 g, 1.43 mmol) was dissolved in water (50 mL) and mixed with pyridine-2-carboxaldehyde (0.27 mL, 2.86 mmol). The solution was stirred for 1 hour and the green-yellow precipitate collected by filtration. The resulting solid was finally washed with water (10 mL) and dried in vacuo. NH2-L. Yield 0.23 g. , 43 %; +ve FAB MS: m/z = 378 (M+1) ; 1H NMR (DMSO-d6, ppm): d 6.00 (s, 1H), 7.14 (d, 4H, J= 8.3 Hz), 7.34 (m, 6H), 7.80 (t, 4H, J= 8.3 Hz), 8.20 (d, 2H, J=7.5 Hz); 8.66 (s, 2H), 8.71 (d, 2H, J=4.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium nitrite; In water; at 5℃; | 50 grams of 90% active 4 4 diamino diphenylamine sulfate is dissolved in 150 MLS of cold water with 50 mis of hydrochloric acid 32%. The solution was iced to 5C and tetrazotized at this temperature by the addition of 55 grams of 40% sodium nitrite solution. When a clear pale yellow solution is obtained excess nitrous acid is reduced with sulfamic acid. To this diazo was added a pre-prepared solution of 25 grams 2,5 dimethoxyaniline dissolved in a mixture of 15 grams of nitric acid 70% and 50 mls of water, which was then cooled to 5C. The coupling was stirred until the tetrazo diphenylamine could no longer be detected in the aqueous phase. 0.15 molar equivalents of essentially mono heptylated 2 naphthol dissolved in 200 mis of toluene was now added to the reaction. A 50% solution of sodium hydroxide was added dropwise until the pH reached 11, which brought the disazo coupling to completion. The pH of the system was then adjusted to 7 with hydrochloric acid, after which 75 mis of hydrochloric acid was added and the temperature adjusted to 20C. 30 grams of a 40% solution of sodium nitrite was now added at 20-25C which rapidly diazotized the pendant amino group. A further 0.15 molar equivalents of heptylated beta naphthol was now added and the pH raised to 4.5 to produce a blackish navy trisazo dye, which separated into the upper organic phase. This was separated and put into a reaction flask. 50 grams of basic copper carbonate was now added, followed by 10 grams of 2 ethyl hexoic acid and 60 grams of 3 amino propyl diethylene glycol. The mixture was heated to 130C WHILE water and solvent distilled out from the system. The cuprification was monitored by TLC, during which process the original dye was converted to a greenish black compound. At the end of the reaction all material volatile to 110C was stripped out under vacuum and the contents of the flask diluted with a equal weight of TOLUENE. The product yielded an intense black shade at 5% solution in an MEK based inkjet ink. The prints from this ink had excellent light fastness and perfect water resistance. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In particular embodiments according to the invention the enhancing agent is selected from the group consisting of: 4-aminophenol; p-Coumaric acid; 4,4'-Biphenol; 3,3',5,5'-Tetramethylbenzidine; 4,4'-Diaminodiphenylamine sulfate; 4,4'-Dimethoxy-N-methyl-diphenylamine; 4,4'-Dihydroxydiphenyl ether; 4-Hydroxy-4'-dimethylamino azobenzene; N'-Benzylidene-N,N-dimethyl-p-phenylenediamine; ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.0% | With sodium hydroxide; In water; | 4,4'-di(benzylthiocarbamoylamino)diphenylamine 4,4'-Diaminodiphenylamine sulfate (1.486 g, 5 mM) was dissolved in 100 ml of water, sodium hydroxide (0.40 g, 10 mM) was added and stirred, and extracted with 150 ml of ethyl acetate. The resulting ethyl acetate solution was thoroughly washed with water, dewatered, and vacuum concentrated to about 20 ml. Precipitated insoluble substances were filtered out, and 2 equivalents of benzylisothiocyanate (1.492 g, 10 mM) were added to the filtrate. The mixture was stirred at 80 C. for 30 minutes, after cooling, the reaction mixture was filtered, and washed with ethyl acetate/n-hexane to obtain 0.97 g (39.0% yield) of a pale pink crystal of compound A-21. Melting point: 179 C. 1 H-NMR (DMSO-d6) ppm delta=4.72 (4H, d, J=5.6, phi-CH2 -- x 2) delta=7.01-7.33 (18H, m, --C6 H4 -- x 2, C6 H5 -- x 2) delta=7.93 (2H, broad s, --CH2 NH-- x 2) delta=8.20 (1H, broad s, --NH--) delta=9.42 (2H, s, --NH-- x 2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.1% | With sodium hydroxide; In water; | 4,4'-di(benzoylthiocarbamoylamino)diphenylamine 4,4'-Diaminodiphenylamine sulfate (1.486 g, 5 mM) was dissolved in 100 ml of water, sodium hydroxide (0.40 g, 10 mM) was added and stirred, and extracted with 150 ml of ethyl acetate. The resulting ethyl acetate solution was thoroughly washed with water, dewatered, and vacuum concentrated to about 20 ml. Precipitated insoluble substances were filtered out, and an ethyl acetate solution of 2 equivalents of benzoylisothiocyanate (1.492 g, 10 mM) was added to the filtrate. The mixture was stirred at room temperature for 30 minutes, the reaction mixture was filtered, and washed with ethyl acetate/n-hexane to obtain 1.60 g (51.1% yield) of a light brown crystal of compound A-22. Melting point: 210 C. 1 H-NMR (DMSO-d6) ppm delta=7.12-8.00 (18H, m, --C6 H4 -- x 2, C6 H5 -- x 2) delta=8.47 (1H, s, --NH--) delta=11.50 (2H, s, --NH-- x 2) delta=12.53 (2H, s, --NH-- x 2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 40% | With hydrogenchloride; ammonium peroxydisulfate; sodium chloride; In water; at 5℃; for 1h; | To synthesize AT3, aniline (1.48 g, 0.016 mol) and 4,-40 -diaminodiphenylamine sulfate (4.73 g, 0.016 mol) were dissolved in HCl aqueous solution (1.0 N, 150 mL) containing 15 g of NaCl. A solution of ammonium persulfate (3.6 g, 0.016 mol) in HCl aqueous solution (1.0 N, 25 mL) was added at a rate of approximately 60 drops min1 to the previously described solution maintained at operational temperature of 5 C using a dropping funnel. The reaction mixture was stirred for 1 h at 5 C. The resulting precipitate was collected through filtration, followed by washing with large amounts of HCl aqueous solution (1.0 N, 400 mL). Then, the filtrate was washed with NH4OH solution (1.0 N, 100 mL) and followed by washing with copious amount of distilled water. Thus, a blue powder was further dried in dynamic vacuum oven at an operational temperature of 50 C for 24 h. The crude product of AT3 was obtained as blue powder with a yield of ~40% |
With hydrogenchloride; ammonium peroxydisulfate; sodium chloride; In water; at 5℃; for 1h; | AT was prepared by following the procedure reported in elsewhere[4]. 75 g of NaCl was dissolved in aqueous HCl solution (1.0 M,800 mL). To this solution, 4,4?-diaminodiphenylamine sulfate (23.65 g,0.796 mol) and aniline (7.40 g, 0.796 mol) were added. To this final solution, HCl (1.0 M, 200 mL) containing ammonium persulfate(18.00 g, 0.789 mol) was added with the help of a dropping funnel at 5 C at the rate of 60 drops/min. The reaction mixture was allowed tostir for 1 h at 5 C. Once the stirring was finished, the reaction mixture was subjected to filtration to collect the precipitate. The obtained precipitate was washed with aqueous HCl solution (1.0 M, 400 mL) andthen precooled to 0 C. Finally, 10% NH4OH solution (100 mL) and alarge amount of distilled water were used to wash the solid product andthen dried in a vacuum oven at 5 C overnight. The aniline trimer (AT)was obtained as a red solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 70℃; for 4h;Inert atmosphere; | 4,4?-diaminodiphenylamine sulfate (5.00 g, 16.82 mmol) and 4-bromotriphenylamine (11.45 g, 35.31 mmol) were suspended in toluene (150 g), and Pd(dba)2 (0.0967 g, 0.168 mmol) as a metal complex catalyst, ligand: t-Bu3P (0.359 mL, 0.135 mmol, 0.375 N (in toluene)), and t-BuONa (8.08 g, 84.08 mmol) as a base were added thereto, and stirred in nitrogen atmosphere, at 70 C. for 4 hours to be reacted. The reaction mixture was filtered, and a saturated saline solution was added to the filtrate to perform separating extraction. After the organic phase was dried over magnesium sulfate, the solvent was removed by distillation to obtain a crude product containing the target product. Then, the target product was recrystallized from 1,4-dioxane. Thus, aniline oligomer compound A was obtained (obtained amount: 7.44 g, yield: 65%). [0118] Note that 1H-NMR of the obtained aniline oligomer compound A was identical to that obtained in Example 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 3.32 g (0. Olmo 1) of A03 and 3.81 g (0.01 mol) of diamino-terminated aniline tetramer, 160 mL of DMF, 25 mL of a mixture of 3.94 g (0. Olmo 1) of the A03 compound were charged with a 500 mL three-necked flask and mechanically stirred at room temperature (30 C) Of deionized water and 30 mL of hydrochloric acid at a molar concentration of 12 M were placed in an ice bath (0 C) at a stirring speed of 80 rpm for 60 minutes; A solution of 2.28 g (0.01 mol) of ammonium persulfate ((NH4) 2S2 08) was dissolved in 40 mL of 1 M hydrochloric acid and placed in a constant pressure dropping funnel into the above mixed solution for 25 minutes. The reaction was carried out under ice bath (0 C) for 2 h.then the mixture was poured into 1500 mL of deionized water and stirred for 30 minutes at a stirring speed of 60 rpm. The filter cake was filtered and the filter cake was dissolved in 700 mL In a molar concentration of 1 M in aqueous ammonia, 16 mL of phenylhydrazine was added and stirred for 10 minutes. Then, 1 M hydrochloric acid was added to adjust the pH to 1, filtered and washed with deionized water. The precipitate was incubated at a vacuum drying temperature of 45 C For 24 hours, and then take the dried precipitate with 1,2-dichloroethane, and then tetrahydrofuran extraction, to be a class of linear aniline oligomer derivatives, known as A04, the structural formula: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 2.14 g (0.0075 mol) of A01 compound and 1.75 g (0.005 mol) of <strong>[53760-27-3]4,4'-diamino-diphenylamine sulfate</strong> were charged at room temperature (25 C) under a mechanical stirrer of 250 mL three-necked flask. DMF, 15 mL of deionized water and 15 mL of hydrochloric acid at a molar concentration of 12 M, placed in an ice bath (0 C) at a stirring speed of 120 rpm and stirred for 30 minutes; 1.14 g (0.005 mol) of ammonium persulfate (NH 4) 2 S 2 O 8) was dissolved in 25 mL of hydrochloric acid having a molar concentration of 1 M and placed in a constant pressure dropping funnel and dropped into the above mixed solution for 15 minutes. (0 C) for 1 h, then the mixture was poured into 750 mL of deionized water and stirred for 30 minutes at a stirring speed of 80 rpm. The filter cake was filtered and the filter cake was dissolved in 300 mL In the presence of 7 mL of phenylhydrazine, and the mixture was added to a solution having a molar concentration of 1 M to adjust the pH to 2, filtered and washed with deionized water. The precipitate was dried at a vacuum drying temperature of 40 C for 48 h hours, and finally the dried precipitate was first extracted with 1,2-dichloroethane and then tetrahydrofuran to give a Class A linear aniline oligomer derivative, designated A02, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 35% | With hydrogenchloride; ammonium peroxydisulfate; In water; N,N-dimethyl-formamide; at 0℃; for 1h; | To prepare AT4, diphenylamine 1.84 g (0.01 mol) and 4,-40 - diaminodiphenyl- amine sulfate (2.1 g, 0.01 mol) were dissolved in a ternary solvent system (100 mL of DMF, 20 mL of distilled water and 15 mL of HCl 1.0 N, 135 mL). A solution of ammonium persulfate (2.28 g, 0.01 mol) in HCl aqueous solution (1.0 N, 25 mL) was added at a rate of approximately 60 drops min1 to the previously described solution at 0 C using a dropping funnel. The reaction mixture was stirred for 1 h at 0 C. It was then transferred into a 1000 mL of beaker containing 700 mL of distilled water to precipitate the product. The precipitate was collected by vacuum filtration through a Buchner funnel and washed by 400 mL of 1.0 N HCl, followed by washing with 100 mL of 1.2 N ammonium hydroxide solution and excess amount of distilled water. After drying at 50 C under dynamic vacuum oven for 24 h, the crude product of AT4 was obtained as blue powder at a yield of ~35% |