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Chemical Structure| 3073-30-1 Chemical Structure| 3073-30-1

Structure of 3073-30-1

Chemical Structure| 3073-30-1

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Product Details of [ 3073-30-1 ]

CAS No. :3073-30-1
Formula : C5H4N4O4
M.W : 184.11
SMILES Code : NC1=NC=C([N+]([O-])=O)C=C1[N+]([O-])=O
MDL No. :MFCD00160298
InChI Key :QNZDCKBBTJYQDT-UHFFFAOYSA-N
Pubchem ID :504340

Safety of [ 3073-30-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H315-H319-H341-H412
Precautionary Statements:P201-P202-P261-P264-P270-P271-P273-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P308+P313-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Computational Chemistry of [ 3073-30-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 46.29
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

130.55 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.09
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

0.71
Log Po/w (WLOGP)?

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

0.49
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.

-1.87
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

-3.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.81

Water Solubility

Log S (ESOL):?

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

-1.64
Solubility 4.23 mg/ml ; 0.023 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.

-3.03
Solubility 0.172 mg/ml ; 0.000934 mol/l
Class?

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

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

-0.43
Solubility 68.6 mg/ml ; 0.372 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.

-6.92 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

2.0 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)

2.43

Application In Synthesis of [ 3073-30-1 ]

* 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 [ 3073-30-1 ]

[ 3073-30-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 3073-30-1 ]
  • [ 3537-14-2 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium sulfide; In methanol; water; at 75℃; 3,5-Dinitropyridin-2-amine (4.0 g, 21.7 mmol) was suspended in methanol (150 mL), and a 20% aqueous solution of ammonium sulfide (31.7 mL, 109 mmol, 5 eq.) was then added. A mixture resulted as the temperature was raised to 75C for 30 minutes. The mixture was allowed to cool and then placed in an ice bath, where a precipitate formed. The solids were collected by filtration, yielding 5-nitropyridine-2,3-diamine (3.4 g, 100%) as a solid. 1H NMR (400 MHz, DMSOd6) delta 8.28-8.29 (m, IH), 7.35-7.37 (m, IH), 6.99 (br s, 2H), 5.32 (br s, 2H).
99% With diammonium sulfide; In methanol; water; at 75℃; for 0.5h; 3,5-Dinitropyridin-2-amine (300.0 mg, 1.63 mmol) and ammonium sulfide solution (2.4 mL, 8.15 mmol) was dissolved in MeOH (11.3 mL), and it was stirred at 75 C. for 30 minutes and then cooled to room temperature. The formed solid was filtered and then dried under reduced pressure to obtain red solid compound of 5-nitropyridine-2,3-diamine (250.0 mg, 99%). [1183] LCMS ESI (+): 155 (M+1) [1184] 1H-NMR (400 MHz, DMSO-d6); delta:8.29 (d, 1H, J=1.8 Hz), 7.36 (d, 1H, J=1.8 Hz), 6.99 (s, 2H), 5.32 (s, 2H)
3.2 g With diammonium sulfide; In methanol; water; for 1h;Reflux; A solution of 3,5-Dinitropyridine-2-amine (3.9 g, 21.2 mmol, 1 eq) in Methanol (80 ml) was treated with 20% aqueous (NH^S (36.1 ml, 106 mmol, 5 eq) and heated to reflux for 1 hour. After cooling, the solid was collected by filtration and dried. The product was used without further purification. Yield: 3.2 g (98%); ESI-MS m/z: 155.0 [M+H]+; HPLC (Gradient A): rt 4.08 min, 100 %; 1H-NMR (DMSO-d6) d: 5.31 (br s, 2H), 6.98 (br s, 2H), 7.36 (d, 1 H, 4J=2.2 Hz), 8.28 (d, 1 H, 4J=2.6 Hz)
  • 2
  • aq. (NH4)2 S [ No CAS ]
  • [ 3073-30-1 ]
  • [ 3537-14-2 ]
YieldReaction ConditionsOperation in experiment
1.092 g (80%) In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; 2,3-Diamino-5-nitropyridine (62) To a suspension of 61 (1.617 g, 8.79 mmol) in MeOH (75 mL) was added 20% aq. (NH4)2 S (15 mL, 44 mmol) dropwise at room temperature with stirring. The resulting dark-red solution was stirred at room temperature for 0.5 h, then refluxed for 0.5 h, then cooled to room temperature. The resulting mixture was filtered. The filtrate was concentrated to about 30 mL and cooled in ice-water. The precipitate was filtered, washed with cooled EtOH (2*5 mL), and dried to give 1.092 g (80%) of 62 as a deep red powder, mp 260-2 C.(dec) (Lit., 260 C., Chemical Abstracts 65:3826 (1966)). 1 H NMR (DMSO-d6): 5.311 (s, 2H), 6.984 (s, 2H), 7.342(d, 1H, J=2.2), 8.171 (d, 1H, J=2.2).
  • 3
  • (NH4)2S [ No CAS ]
  • [ 3073-30-1 ]
  • [ 3537-14-2 ]
YieldReaction ConditionsOperation in experiment
In methanol; 2,3-Diamino-5-nitropyridine (3). To a stirred suspension of 2-Amino-3,5-dinitropyridine (2) (1.62g, 8.8 mmol) in MeOH (75 mL) was added an aqueous solution of (NH4)2S (20%, 15 mL, 44 mmol) dropwise at room temperature over 20 minutes. The mixture was stirred for an additional 30 minutes at room temperature and then heated at reflux for 30 minutes. The solution was cooled to room temperature and the solid collected by filtration, rinsed with cold MeOH (2*20 mL), and dried in vacuo at room temperature to give 3 as a red solid (0.812 g, 5.27 mmol, 60%). 1H NMR (500 MHz, DMSO-d6) delta5.31 (s, 2H), 6.98 (s, 2H), 7.35 (d, J=2.55 Hz, 1H), 8.28 (d, J=2.91 Hz, 1H). EIMS M+1 155.1.
In methanol; 2,3-Diamino-5-nitropyridine (3). To a stirred suspension of 2-Amino-3,5-dinitropyridine (2) (2 g, 10.8 mmol) in MeOH (75 mL) was added an aqueous solution of (NH4)2S (20%, 19 mL) dropwise at room temperature over 20 minutes. The mixture was stirred for an additional 30 minutes at room temperature and then heated at reflux for 30 minutes. The solution was cooled to room temperature and the solid collected by filtration, rinsed with cold MeOH (2*20 mL), and dried in vacuo at room temperature to give 3 as a red solid (1.31 g, 8.5 mmol, 79%). 1H NMR (500 MHz, DMSO-d6) 65.31 (s, 2H), 6.98 (s, 2H), 7.35 (d, J=2.55 Hz, 1H), 8.28 (d, J=2.91 Hz, 1H). EIMS M+1 155.1.
 

Historical Records

Technical Information

Categories

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