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CAS No. : | 136-17-4 | MDL No. : | MFCD00025285 |
Formula : | C12H13N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VOSLIUIVGWBSOK-UHFFFAOYSA-N |
M.W : | 199.25 | Pubchem ID : | 8683 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 64.79 |
TPSA : | 64.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.02 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | 2.1 |
Log Po/w (WLOGP) : | 2.61 |
Log Po/w (MLOGP) : | 2.07 |
Log Po/w (SILICOS-IT) : | 1.27 |
Consensus Log Po/w : | 1.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.86 |
Solubility : | 0.276 mg/ml ; 0.00139 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.08 |
Solubility : | 0.167 mg/ml ; 0.00084 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.25 |
Solubility : | 0.0111 mg/ml ; 0.0000558 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.29 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501 | UN#: | N/A |
Hazard Statements: | H302+H312+H332 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 lead dioxide | ||
1.11 g | With magnesium sulfate In nitrobenzene for 24h; Reflux; | 4.2.1 General procedure for the synthesis of intermediates A and B Compound A was immediately refluxed for 24 h in nitrobenzene (100 mL) containing MgSO4 in a flask. After nitrobenzene removal in vacuo, and the residue was quenched with water, extracted with dichloromethane and dried over anhydrous Na2SO4. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography, using petroleum ether/ethyl acetate, 3:1-1:1. The product phenazin-2-amine (B) was obtained as a red solid (1.11 g, 30%): mp 285-286 °C (lit. mp 280 °C) [25] . IR (KBr, cm-1): 3309, 3194, 2918, 1640, 1597, 1514, 1476, 1453, 1335, 1232, 1132, 827, 755. 1H NMR (DMSO-d6, 500 MHz) δ: 8.06-8.04 (d, J = 8.5 Hz, 1H, Ar-H), 7.99-7.97 (d, J = 8.5 Hz, 1H, Ar-H), 7.91-7.89 (d, J = 9.2 Hz, 1H, Ar-H), 7.78-7.75 (t, J = 7.5 Hz, 1H, Ar-H), 7.67-7.64 (t, J = 7.5 Hz, 1H, Ar-H), 7.46-7.44 (d, J = 9.2 Hz, 1H, Ar-H), 6.91 (s, 1H, Ar-H), 6.47 (s, 2H, NH2). 13C NMR (DMSO-d6, 125 MHz) δ: 151.0 (Ar-C), 145.8 (Ar-C), 143.2 (Ar-C), 139.7 (Ar-C), 139.3 (Ar-C), 130.1 (Ar-C), 130.0 (Ar-C), 129.2 (Ar-C), 128.0 (Ar-C), 127.0 (Ar-C), 126.7 (Ar-C), 101.2 (Ar-C). HRMS (ESI): m/z [M + H]+ calcd for C12H9N3: 196.08747, found: 196.08707. |
With magnesium sulfate; nitrobenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; formic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Benzoylierung das Hydrochlorid; | ||
bei Benzoylierung; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With hydrazine In tetrahydrofuran; ethanol at 20℃; for 0.333333h; | To a solution of 2, 4-DINITROPHENYLAMINE (1.5 g, 5.8 MMOL) in ethanol-THF (150: 50 mL) were added hydrazine hydrate (2 mL, 65 MMOL) and Raney Nickel (2.0 g). The reaction mixture was stirred at rt for 20 min, filtered through Celite. Evaporation of the solvent gave a black residue, which was purified by flash chromatography (methanol-DCM gradient elution). A black crystalline solid (1.0 g, 87%) was obtained. Mp 128-129°C ; TLC single spot at Rf 0.46 (8% METHANOL/DCM) ; 1H NMR (270 MHz, DMSO) : 5 7.25 (2H, t, J = 7.5 Hz, ArH), 6.73 (1H, s, NH), 6.61 (1H, d, J = 8. 3 Hz, ArH), 6.49-6. 55 (3H, m, ArH), 5.99 (1H, d, J = 2.5 Hz, ArH), 5.83 (1H, dd, J = 8. 2,2. 5 Hz, ArH), 4.66 (2H, s, NH2), 4.44 (2H, s, NH2) ; APCI-MS 198 (M-H+). |
With hydrogenchloride; iron | ||
With hydrogenchloride; tin |
With ethanol; iron; acetic acid | ||
With ammonium chloride; iron | ||
With hydrogen In ethyl acetate | ||
With 5%-palladium/activated carbon; hydrogen In ethyl acetate for 24h; | 4.2.1 General procedure for the synthesis of intermediates A and B N-(2,4-Dinitrophenyl)benzeneamine (5.0g, 19.3mmol) was dissolved in ethyl acetate (300mL), then catalytically reduced in a Parr apparatus for 24h using a 5% Pd/C catalyst under hydrogen atmosphere. After reduction, the reaction mixture was filtered into ethyl acetate. The solvent was removed in vacuo, giving the desired N1-phenylbenzene-1,2,4-triamine A (3.76g, 18.9mmol, 98%), which was used without further purification. Compound A was immediately refluxed for 24h in nitrobenzene (100mL) containing MgSO4 in a flask. After nitrobenzene removal in vacuo, and the residue was quenched with water, extracted with dichloromethane and dried over anhydrous Na2SO4. The solvent was removed under vacuum and the residue was purified by silica gel column chromatography, using petroleum ether/ethyl acetate, 3:1-1:1. The product phenazin-2-amine (B) was obtained as a red solid (1.11g, 30%): mp 285-286°C (lit. mp 280°C) [25]. | |
With hydrogen In ethyl acetate at 20℃; | 1.2 [0118] Step 2:To a solution of crude starting material from step 1 in EtOAc was added a scoop of 10% Pd/C (~50 mg). The vial was sealed, flushed with Argon, and then placed under H2 balloon. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through a pad of Celite and eluted with EtOAc. The solvent was removed in vacuo and crude material was carried forward without purification. | |
With palladium on activated charcoal; hydrogen |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; acetic acid; zinc |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol Versetzen mit Eisenchlorid-Loesung und Behandeln des Eisenchlorid-Doppelsalzes mit Ammoniak; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid isoliert als Chlorid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. m. KBrO3, chemischer Oszillator; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; bromate In water chemical oscillation with and without a catalyst; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Et3N / dimethylformamide 2: aq. HCl / 100 °C 3: phenol / 110 - 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / dimethylformamide 2: aq. HCl / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: alcohol 2: methanol; zinc; glacial acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: alcohol 2: methanol; zinc; glacial acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 2,4-diaminodiphenylamine; acetic anhydride With acetic acid at 80℃; for 6h; Stage #2: With sodium hydrogencarbonate In water at 20℃; | N'-PHENYL-BENZENE-1, 2,4-triamine (800 mg, 4 MMOL) was dissolved in acetic acid (10 mL), acetic anhydride (1.0 mL) was added to the solution. The mixture was stirred at 80°C for 6h, cooled to rt and neutralized with 5% sodium carbonate, then extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and concentrated to give a residue, which was crystallized from ethanol. A brown crystalline solid (0.85 g, 80%) was obtained. Mp 231-232°C ; TLC single spot at Rf 0.39 (10% methanol/DCM) ;'H NMR (270 MHz, DMSO): 8 9.92 (1H, s, NH), 7.97 (1H, d, J = 1.6 Hz, ArH), 7.51-7. 67 (5H, m, ArH), 7.31 (1H, dd, J = 8.3, 1.9 Hz, ArH), 7.04 (1H, d, J = 8.3 Hz, ArH),, 2. 41 (3H, s, CH3), 2.05 (3H, s, CH3) ; APCI-MS 264 (M-H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Among these anilinoamines, the following compounds are most preferred: 4-Methoxy-2-methylaniline; 4-Anilino-m-phenylenediamine; 4-Cyclohexylaniline; m-Anilinophenol; 2-Aminoacetophenone; ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride at 110℃; | |
Stage #1: formic acid; 4-anilino-m-phenylenediamine With hydrogenchloride In water monomer at 100℃; for 1.5h; Stage #2: With sodium hydroxide In water monomer at 20℃; | 1.3 [0119] Step 3:The crude material from step 2 was suspended in 4N HCI (2ml) and formic acid (0.5 ml). The mixture was heated to 1000C for 1.5 hours. The reaction was cooled to room temperature and 5 N NaOH was added to adjust pH to ~13. The mixture was extracted with DCM (3x 5ml). The combined organic layers were dried over MgSO-j, filtered, and solvent evaporated in vacuo to give the crude product that was carried forward without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: 1,5-difluoro-2,4-dinitrobenzene; 2,4-diaminodiphenylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 2h; Stage #2: orcinol In N,N-dimethyl-formamide at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 85℃; for 18h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: 1,5-difluoro-2,4-dinitrobenzene; 2,4-diaminodiphenylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 2h; Stage #2: 1-carbomethoxy-3,5-dihydroxybenzene In N,N-dimethyl-formamide at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: 1,5-difluoro-2,4-dinitrobenzene; 2,4-diaminodiphenylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 2h; Stage #2: Ethyl gallate In N,N-dimethyl-formamide at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: 1,5-difluoro-2,4-dinitrobenzene; 2,4-diaminodiphenylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 2h; Stage #2: methyl 3,5-diaminobenzoate In N,N-dimethyl-formamide at 85℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | at 70℃; for 16h; | 2. General Procedure A General procedure: In a screw-cap vial, the diamine or aminothiophenol (1 mmol) was dissolved in fluorinated carboxylic acid (2 mL, 0.5 M) and the reaction was stirred at 70 °C for 16 hours. The fluorinated carboxylic acid was then evaporated under reduced pressure and the crude product was purified by silica gel column chromatography to yield the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / N,N-dimethyl-formamide; triethylamine / 2.5 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 1 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: magnesium sulfate / nitrobenzene / 24 h / Reflux 2: pyridine / dichloromethane; pyridine / 0.5 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With Recombinant CotA-laccase from Bacillus subtilis In methanol; aq. phosphate buffer at 37℃; for 24h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate / tetrahydrofuran / 48 °C 2: hydrogen / palladium 10% on activated carbon / ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nitrobenzene; magnesium sulfate 2: pyridine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nitrobenzene; magnesium sulfate 2: pyridine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nitrobenzene; magnesium sulfate 2: pyridine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nitrobenzene; magnesium sulfate 2: pyridine / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 110 °C 2.1: acetic acid / methanol / 20 °C 2.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 110 °C 2.1: acetic acid / methanol / 20 °C 2.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 110 °C 2.1: acetic acid / methanol / 20 °C 2.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 110 °C 2.1: acetic acid / methanol / 20 °C 2.2: 0 - 20 °C |
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