13505-02-7|4-Nitropyridin-3-amine| Ambeed

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Quality Control of [ 13505-02-7 ] Purity: 95% SDS Specification

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Product Details of [ 13505-02-7 ]

CAS No. :	13505-02-7
Formula :	C₅H₅N₃O₂
M.W :	139.11
SMILES Code :	O=[N+](C1=C(N)C=NC=C1)[O-]
MDL No. :	MFCD04114232
InChI Key :	SXIUYRNIWXQXEA-UHFFFAOYSA-N
Pubchem ID :	586943

Safety of [ 13505-02-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 13505-02-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	37.46
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	84.73 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.74
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.55
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.58
Log P_o/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.	-0.53
Log P_o/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	-1.44
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.43
Solubility	5.2 mg/ml ; 0.0374 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.	-1.9
Solubility	1.75 mg/ml ; 0.0126 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	-1.02
Solubility	13.3 mg/ml ; 0.0957 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.	-6.76 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)	1.92

Application In Synthesis of [ 13505-02-7 ]

* 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 [ 13505-02-7 ]

[ 13505-02-7 ] Synthesis Path-Downstream 1~13

1
[ 15862-54-1 ]
[ 13269-19-7 ]
[ 13505-02-7 ]

References: [1]Acta Chimica Hungarica,1983,vol. 113,p. 159 - 164.

2
[ 1122-61-8 ]
[ 13505-02-7 ]

References: [1]Chemical Communications,1998,p. 1519 - 1520.

Yield	Reaction Conditions	Operation in experiment
31%		Example 16 43 mg of 3-amino-4-nitropyridine was obtained according to the same manner as that described in Example 15 except for using zinc pyrithione (317 mg, 1 mmol) in place of zinc (II) chloride (yield: 31%).
31%		Example 18 43 mg of 3-amino-4-nitropyridine was obtained according to the same manner as that described in Example 15 except for using lithium amide (69 mg, 3 mmol in place of potassium tert-butoxide (yield: 31%).
28%		Example 17 39 mg of 3-amino-4-nitropyridine was obtained according to the same manner as that described in Example 15 except for using zinc naphthenate (817 mg) in place of zinc (II) chloride (yield: 28%).

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[ 13505-02-7 ]
[ 107-13-1 ]
C₈H₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-benzyl-trimethylammonium hydroxide; In 1,4-dioxane; at 20℃; for 24 - 96h;	An aminonitropyridine derivative II, such as <strong>[13505-02-7]3-amino-4-nitropyridine</strong>, may be treated with a mixture of acrylonitrile and a suitable base such as Triton B (N-benzyltriethylammonium hydroxide) in an appropriate solvent such as dioxane at room temperature for 1-4 days to give the illustrated nitrile derivative III. Treatment of derivative III with a suitable reduction catalyst such as Pd/C in an appropriate solvent such as ethyl acetate under hydrogen atmosphere of about 50-60 psig for about 3-12h gives the amino derivative IV. This derivative may be heated with ethyl ethoxycarbonylacetimidate hydrochloride in a suitable solvent such as EtOH for about 4-24 h to give the the ester V. Treatment of derivative V with an anhydrous acid such as HCl(g) in an appropriate solvent such as EtOH at reflux for 4-24 h gives the diester VI. This diester may be treated with a suitable base such as sodium ethoxide in an appropriate solvent such as EtOH for about 12-24 h at room temperature followed by treatment with ethanolic HCl to give the derivative VII Derivative VII is heated to reflux with the appropriate substituted amine derivative VIII, such as 3-amino-1,2,4-triazole, in a suitable solvent such as xylene for about 1-24 h to give compounds of formula I, the amide derivatives IX. These compounds may be selectively alkylated in the N5 position using the method Mitsunobu (see Hughes, D. Organic Reactions, 42, 355-656) or the recently reported modified procedures (see Tsunoda,Tetrahedron Letters 1993, 34, 1639-1642 and Tsunoda, Chemistry Letters 1994, 539-542). Treatment of compounds IX with an appropriately substituted alcohol such as benzylalcohol and 1-5 equivalents of a suitable activating agent such as diethylazodicarboxylate (DEAD), azodicarbonyldipiperidine (ADDP), or 1,1-azobis(N,Ndimethylformamide) (TMAD) and an appropriate trisubstituted phosphine such as triphenylphosphine or tributylphosphine in an appropriate solvent such as benzene, THF, or DMF at about 0 degress C to room temperature for about 1-24 hr can provide the desired N5-substituted pyrrolobenzimidazopyridine derivatives X.

References: [1]Patent: EP1023291,2004,B1 .Location in patent: Page 4-5.

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[ 67-62-9 ]
[ 1122-61-8 ]
[ 7646-85-7 ]
[ 13505-02-7 ]

Yield	Reaction Conditions	Operation in experiment
25%	With ammonium chloride; potassium tert-butylate; In N,N-dimethyl-formamide;	Example 15 4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25 C. After completion of the addition, the resulting mixture was at 25 C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

References: [1]Patent: US5648496,1997,A .

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[ 21739-92-4 ]
[ 13505-02-7 ]
[ 1258281-56-9 ]