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Chemical Structure| 608-32-2 Chemical Structure| 608-32-2

Structure of 608-32-2

Chemical Structure| 608-32-2

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Product Details of [ 608-32-2 ]

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

Safety of [ 608-32-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H304-H410
Precautionary Statements:P301+P310-P331-P405
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 608-32-2 ] Show Less

Physicochemical Properties

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
Ertl P. et al. 2000 J. Med. Chem.

78.06 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.37
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.53
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.46
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.18
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.04

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.76
Solubility 21.3 mg/ml ; 0.173 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.64
Solubility 28.2 mg/ml ; 0.229 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.27
Solubility 6.54 mg/ml ; 0.0531 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.43 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.07

Application In Synthesis of [ 608-32-2 ]

* 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 [ 608-32-2 ]

[ 608-32-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 103-82-2 ]
  • [ 608-32-2 ]
  • 2-benzyl-1(3)<i>H</i>-benzimidazol-4-ylamine [ No CAS ]
  • 2
  • [ 608-32-2 ]
  • [ 517-21-5 ]
  • [ 16566-20-4 ]
  • 3
  • [ 608-32-2 ]
  • [ 767-65-7 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 602-03-9 ]
  • [ 608-32-2 ]
YieldReaction ConditionsOperation 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)+.
  • 5
  • [ 606-22-4 ]
  • [ 608-32-2 ]
YieldReaction ConditionsOperation 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.
  • 6
  • [ 618-77-9 ]
  • [ 608-32-2 ]
  • 7
  • [ 618-77-9 ]
  • [ 608-32-2 ]
  • [ 15719-64-9 ]
  • 8
  • [ 608-32-2 ]
  • [ 64-19-7 ]
  • [ 30905-08-9 ]
  • 9
  • [ 608-32-2 ]
  • [ 64-19-7 ]
  • [ 96013-05-7 ]
  • 10
  • [ 608-32-2 ]
  • [ 65-85-0 ]
  • 2-phenyl-1(3)<i>H</i>-benzimidazol-4-ylamine [ No CAS ]
  • 11
  • [ 608-32-2 ]
  • [ 64-18-6 ]
  • [ 137654-47-8 ]
  • 12
  • [ 608-32-2 ]
  • [ 131543-46-9 ]
  • [ 16566-20-4 ]
  • 14
  • [ 608-32-2 ]
  • [ 333-20-0 ]
  • [ 137697-81-5 ]
  • 15
  • [ 608-32-2 ]
  • [ 79591-73-4 ]
  • [ 79591-92-7 ]
  • 16
  • [ 608-32-2 ]
  • [ 31616-72-5 ]
  • 10-amino-4,6-dimethyl-5,2,8-ethanylylidene-5H-1,9-benzodiazacycloundecine [ No CAS ]
  • 17
  • [ 7647-01-0 ]
  • [ 16322-19-3 ]
  • tin [ No CAS ]
  • [ 608-32-2 ]
YieldReaction ConditionsOperation 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...
  • 20
  • [ 7647-01-0 ]
  • [ 88-88-0 ]
  • tin [ No CAS ]
  • [ 608-32-2 ]
  • 21
  • [ 608-32-2 ]
  • [ 74071-23-1 ]
  • 26
  • [ 608-32-2 ]
  • [ 84-11-7 ]
  • [ 860478-79-1 ]
YieldReaction ConditionsOperation 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
  • 27
  • [ 608-32-2 ]
  • [ 126-81-8 ]
  • [ 928388-13-0 ]
YieldReaction ConditionsOperation 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).
  • 28
  • [ 66046-54-6 ]
  • [ 608-32-2 ]
  • 29
  • [ 608-32-2 ]
  • [ 91-56-5 ]
  • [ 1097635-50-1 ]
  • 30
  • [ 30417-18-6 ]
  • [ 608-32-2 ]
  • 31
  • [ 30417-18-6 ]
  • [ 608-32-2 ]
  • [ 1097635-52-3 ]
  • 32
  • [ 3694-52-8 ]
  • [ 608-32-2 ]
YieldReaction ConditionsOperation 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.
  • 33
  • [ 608-32-2 ]
  • 3-ethoxy-4-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-ylamino)cyclobut-3-ene-1,2-dione [ No CAS ]
  • 34
  • [ 608-32-2 ]
  • 3-[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-4-(2-oxo-2,3-dihydro-1H-benzoimidazol-4-ylamino)cyclobut-3-ene-1.2-dione [ No CAS ]
  • 35
  • [ 608-32-2 ]
  • [ 530-62-1 ]
  • [ 75370-65-9 ]
YieldReaction ConditionsOperation 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.
 

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Technical Information

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