Structure of 608-32-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 608-32-2 |
Formula : | C6H9N3 |
M.W : | 123.16 |
SMILES Code : | NC1=CC=CC(N)=C1N |
MDL No. : | MFCD01326518 |
InChI Key : | RUOKPLVTMFHRJE-UHFFFAOYSA-N |
Pubchem ID : | 69099 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H304-H410 |
Precautionary Statements: | P301+P310-P331-P405 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 3.0 |
Molar Refractivity | 39.66 |
TPSA ? Topological Polar Surface Area: Calculated from |
78.06 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.37 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.53 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.18 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.04 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.76 |
Solubility | 21.3 mg/ml ; 0.173 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.64 |
Solubility | 28.2 mg/ml ; 0.229 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.27 |
Solubility | 6.54 mg/ml ; 0.0531 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
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 |
-7.43 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.07 |
* 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 |
---|---|---|
56% | With selenium(IV) oxide; In ethanol; water; at 20℃; for 0.25h; | To a solution of 1 g (5.0 mmol) of 1 ,2,3-triaminobenzene dihydrochloride X-6c in water (1 0ml) was added a solution of Se02 (555 mg, 5.0 mmol) in water (15 ml) at room20 temperature. After the addition was finished the reaction mixture was stirred for 15 minand then alkalized with a 30percent aq. NaOH solution while cooling on an ice bath. Theresulting orange needles were filtered off under reduced pressure, washed with water anddried. Additional purification by column chromatography (eluent: pure dichloromethane)yielded 560 mg of 4-amino-2, 1 ,3-benzoselenodiazole.25 Yield: 56percent.1H NMR (600 MHz, DMSO-d5) o: 7.26 (dd, J = 8.9, 7.2 Hz, 1 H), 6.93 (d, J = 8.8 Hz, 1 H),6.35 (d, J = 7.3 Hz, 1 H), 5.98 (s, 2H, NH2).Purity> 95 percent, calculated from 1H NMR data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogen;palladium on activated charcoal; | Example 40: synthesis of [6-Amino-l l-(4-benzyloxy-2-fluorophenyl)-3,3-dimethyl- 1 , 1 -dioxo- 1,2,3,4,5,11 -hexahydro- 1 lambda6-thia-5 , 1 Q-diaza-dibenzo[a,dlcyclohepten- 10-yl]- (6-methylpyridin-2-yl)-methanone (353); A solution of 2,3-dinitroaniline (10 g, 54.61 mmol) was catalytically hydrogenated on Pd/C to yield, after filtration and concentration to dryness, 6420 mg (95percent yield) of the target product (349); m/z = 124 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium tetrahydroborate; In water; at 20℃; for 0.25h; | General procedure: In a typical procedure, a mixture of nitrobenzene (2 mmol), NaBH4 (6 mmol), Fe3O4/Ala-AA-Ni (0.03 g) and water (3 mL) was placed in a round bottom flask. The suspension was stirred at room temperature. The reaction process was monitored by thin layer chromatography (TLC). At the end of the reaction, the residue was extracted with diethyl ether. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Pure product was obtained by column chromatography over silica gel using hexane/ethyl acetate as eluent. The products were identified with 1H NMR, 13C NMR and FT-IR spectroscopy techniques. |
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; at 20℃; for 15.0h; | 15.0 g (82 mmol) of 2,6-dinitroaniline was dissolved in 150 g of THF and the reaction system was satisfactorily purged with nitrogen, to which 7.6 g of 5percent Pd/C (hydrous) was added. Thereafter, the system was purged with hydrogen, followed by reaction at room temperature for 15 hours. After completion of the reaction, the reaction solution was filtered to remove Pd therefrom, and the resulting filtrate was condensed as it is to obtain the intended product. The thus obtained product was instable and was used as it is in a subsequent reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The following list of illustrative compounds is therefore to be read in the light of the above teachings.Aliphatic and Alicyclic Aminesmethylaminen-butylaminetetramethylammonium chloride...1,2-diaminocyclobutane1,4-diaminocyclohexanephenylenediaminetriaminobenzene3,3'-diaminobiphenylallylaminediallylamine... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; acetic acid; at 70℃; for 2.0h; | 10.1 g (82 mmol) of <strong>[608-32-2]1,2,3-triaminobenzene</strong> and 4.6 g (70 mmol) of 9,10-phenanthrenequinone were placed in a four-necked flask, to which 350 g of a solvent of acetic acid and methanol at 1:1 was added for dissolution, followed by reaction at a reaction temperature of 70°C for 2 hours. After the reaction, the solvent was removed and the resulting product was washed with methanol to obtain the intended product. Yield: 17.1 g Ocher solid m/z: 295 (calculated: 295.11) 13C-NMR: 146.932, 144.145, 143.084, 139.740, 133.473, 133.007, 132.656, 132.213, 131.602, 131.488, 130.847, 130.473, 128.465, 126.869, 126.831, 126.663, 123.900, 116.243, 108.647 ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In toluene; for 12.0h;Heating / reflux; dean stark apparatus; | A mixture of v-1 (0.0089 mol) and v-2 (0.0089 mol) in toluene (50 ml) was stirred and refluxed for 12 h in a Dean Starck apparatus, then cooled to room temperature. The precipitate was filtered, washed with diethyl ether and dried, yielding: 2 g of v-3 (100percent).A mixture of v-3 (0.0106 mol) and v-4 (0.0106 mol) in AcOH (2.6 ml) and EtOH (50 ml) was stirred at 750C for 24 hours, then cooled to room temperature and concentrated under reduced pressure. The residue was taken up in CH2Cl2. The organic layer was washed with K2C O3 10percent, dried (over MgSO4), filtered and the solvent was evaporated. The residue (5.7 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 100/0/0 to 99/1/0.1). Three fractions were collected and the EPO <DP n="118"/>solvent was evaporated, yielding: 0.27 g of v-5 (4.5percent) (melting point > 2600C), 0.4 g of v-6 (6.7percent) and 0.34 g of v~7 (5.7percent) (melting point > 2600C).A mixture of v-6 (0.0006 mol) and NH2-NH2/H2O (0.003 mol) in EtOH (20 ml) was stirred and refluxed for 6 hours, then concentrated under reduced pressure. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding: 0.12 g (50percent). Part of this fraction (0.04 g) was crystallized from CH3CN. The precipitate was filtered off and dried, yielding: 0.03 g of v-8 (melting point: 248°C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; hydrogen; In methanol; for 1.5h; | Step 1 Benzene-1,2,3-triamine A solution of 3-nitrobenzene-1,2-diamine at 0.05 mol/1 in methanol was passed through an H-Cube reactor on a cartridge of palladium on carbon with a flow rate of 1 ml/min. After one and a half hours, the product was completely hydrogenated. The solvent was concentrated. 450.7 g of benzene-1,2,3-triamine were obtained in the form of a green oil. Yield>100percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In acetonitrile; at 20 - 70℃; | Step 2 4-Amino-1,3-dihydrobenzoimidazol-2-one 0.53 g (6.5 mmol, 2 eq) of N-N'-carbonyliimidazole were added portionwise to 450.7 mg (3.24 mmol, 1 eq) of <strong>[608-32-2]benzene-1,2,3-triamine</strong> in solution in 30 ml of acetonitrile. The reaction medium was stirred at ambient temperature for 6 hours and then heated at 70° C. overnight. The reaction was stopped by adding 50 ml of water and then extracted with ethyl acetate. The organic phases were combined, and dried over sodium sulfate. The solvents were evaporated off and then the residue was purified by chromatography on silica gel (dichloromethane/methanol/aqueous ammonia: 95/5/2). 229.9 mg of 4-amino-1,3-dihydrobenzoimidazol-2-one were obtained. Yield=42percent. |
A804054 [638-09-5]
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