1137475-57-0|2-Bromo-4-chloro-5-nitropyridine| Ambeed

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Quality Control of [ 1137475-57-0 ] Purity: 95% SDS Specification

COA

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NMR

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Product Details of [ 1137475-57-0 ]

CAS No. :	1137475-57-0
Formula :	C₅H₂BrClN₂O₂
M.W :	237.44
SMILES Code :	O=[N+](C1=CN=C(Br)C=C1Cl)[O-]
MDL No. :	MFCD17014975
InChI Key :	HJWNYVVSEUNNMO-UHFFFAOYSA-N
Pubchem ID :	59613418

Safety of [ 1137475-57-0 ]

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

Computational Chemistry of [ 1137475-57-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	45.77
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.71 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.28
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	2.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.41
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.	1.47
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	0.62
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.12
Solubility	0.181 mg/ml ; 0.000763 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.2
Solubility	0.149 mg/ml ; 0.000628 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	-2.88
Solubility	0.312 mg/ml ; 0.00132 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	Yes
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	Yes
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.	-6.09 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	0.0
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	3.0 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)	2.18

Application In Synthesis of [ 1137475-57-0 ]

* 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 [ 1137475-57-0 ]

[ 1137475-57-0 ] Synthesis Path-Downstream 1~35

1
[ 1137475-57-0 ]
[ 2393-23-9 ]
[ 1184842-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; for 1.5h;	Synthesis 1-1 -A N-(4-Methoxybenzyl)-2-bromo-5-nitropyridin-4-amine A solution of 4-methoxybenzylamine (0.756 g, 5.51 mmol) in acetonitrile (2 mL) was added to a mixture of <strong>[1137475-57-0]2-bromo-4-chloro-5-nitropyridine</strong> (1.19 g, 5.01 mmol) and triethylamine (0.768 mL, 5.51 mmol) in acetonitrile (8 mL). After stirring for 1.5 hours, the solution was diluted with ethyl acetate (100 mL) which was then washed successively with water and brine before being concentrated in vacuo to a light brown oil which solidified on standing to give the title compound (1.31 g, 3.87 mmol, 77%). 1H NMR (d6- DMSO, 400 MHz) delta 9.00 (br t, 1 H, J = 6.3 Hz), 8.80 (s, 1 H)1 7.35 (d, 2H, J = 8.7 Hz), 7.10 (s, 1 H), 6.95 (d, 2H, J = 8.8 Hz), 4.60 (d, 2H, J = 6.0 Hz), 3.70 (s, 3H). LCMS (1) Rt = 2.13 min; m/z (ESI-) 336, 338 (M-H).

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.
[2]Patent: WO2009/103966,2009,A1 .Location in patent: Page/Page column 82.

2
[ 1137475-57-0 ]
[ 162167-97-7 ]
[ 1137476-56-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In acetonitrile; for 1h;	A solution of 3-(aminomethyl)-1-boc-piperidine (409 mg, 1.91 mmol) in acetonitrile (2.5 mL) was added dropwise to a solution of <strong>[1137475-57-0]2-bromo-4-chloro-5-nitropyridine</strong> (431 mg, 1.82 mmol) and triethylamine (0.28 mL, 2.0 mmol) in acetonitrile (10 mL). The solution was stirred for 1 hr then partitioned between dichloromethane and water. The aqueous phase was extracted with dichioromethane (x3) and the combined organic phases were dried (Na2SO4) and concentrated to give tert-butyl 3-((2-bromo-5-nitropyridin-4- ylamino)methyl)piperidine-1-carboxylate as a yellow-brown solid (718 mg, 95percent) which was used without further purification.LCMS (1 ): Rt = 2.38 min; m/z (ESI+) 415, 417 (MH+).

References: [1]Patent: WO2009/44162,2009,A1 .Location in patent: Page/Page column 185-186.

3
[ 1137475-57-0 ]
[ 123855-51-6 ]
[ 1137476-28-8 ]

Yield	Reaction Conditions	Operation in experiment
62%		N-Boc-4-piperidinemethanol (860 mg, 4.0 mmol) was added to a suspension of 60% sodium hydride (160 mg, 4.0 mmol) in DMF (40 mmol) at room temperature. After 20 minutes, <strong>[1137475-57-0]2-bromo-4-chloro-5-nitropyridine</strong> (949 mg, 4.0 mmol) was added in one portion, and the resulting mixture was stirred overnight at room temperature. The mixture was diluted with ether and washed with water. The aqueous phase was extracted with ether. The combined organic phases were washed with water and brine, then dried (Na2SO4) and concentrated. Silica column chromatography, eluting with 20% ethyl acetate - hexane, gave tert-butyl 4-((2-bromo-5-nitropyridin-4-yloxy)methyl)piperidine-1-carboxylate (789 mg, 62%) as a viscous, pale yellow oil which solidified on standing.1H NMR (CDCI3, 400MHz) delta 8.80 (s, 1H), 7.20 (s, 1H)7 4.05-4.15 (m, 2H), 4.00 (d, 2H, J = 6.3 Hz), 2.75-2.85 (m, 2H), 2.10 (m, 1H), 1.80-1.90 (m, 2H), 1.45 (s, 9H), 1.20-1.30 (m, 2H). LCMS (1 ) Rt = 2.45 min; m/z (ESI+) 316, 318 (MH+),

References: [1]Patent: WO2009/44162,2009,A1 .Location in patent: Page/Page column 175.

4
[ 1137475-57-0 ]
[ 144222-22-0 ]
[ 1137475-56-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In acetonitrile; for 0.516667h;	A solution of 4-(aminomethyl)-1-boc-pipeiotadine (370 mg, 1.73 mmol) in acetonitrile (1 ml_) was added over 1 minute to a solution of <strong>[1137475-57-0]2-bromo-4-chloro-5-nitropyridine</strong> (373 mg, 1.57 mmol) and triethylamine (0.24 mL, 1.73 mmol) in acetonitrile (5 mL). The solution was stirred for 30 minutes then partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane (x3) and the combined organic phases were dried (Na2SO4) and concentrated to give tert-butyl 4-((2-bromo-5-nitropyridin-4- ylamino)methyl)piperidine-1-carboxylate as a light brown foam (640 mg, 98%) which was used without further purification.1H NMR (MeOD, 400MHz) delta 8.82 (s, 1 H), 7.25 (s, 1 H), 4.14 (m, 3H), 3.35 (s, 1H), 1.97- 1.88 (m, 1H), 1.80 (m, 3H), 1.27-1.17 (m, 3H). LCMS (1) Rt = 2.35 min; m/z (ESI+) 415, 417 (MH+).

References: [1]Patent: WO2009/44162,2009,A1 .Location in patent: Page/Page column 146.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.

5
[ 1137475-57-0 ]
C₃₀H₃₄N₈O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.

6
[ 1137475-57-0 ]
[ 1184843-67-1 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.
[2]Patent: WO2009/103966,2009,A1 .

7
[ 1137475-57-0 ]
[ 1184843-69-3 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.

8
[ 1137475-57-0 ]
[ 1184843-63-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.
[2]Patent: WO2009/103966,2009,A1 .

9
[ 1137475-57-0 ]
[ 1184843-64-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.
[2]Patent: WO2009/103966,2009,A1 .

10
[ 1137475-57-0 ]
[ 1184843-65-9 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.
[2]Patent: WO2009/103966,2009,A1 .

11
[ 1137475-57-0 ]
[ 144222-22-0 ]
[ 1351533-49-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8328 - 8342.

12
[ 1137475-57-0 ]
5-(5-amino-4-(piperidin-4-ylmethylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile [ No CAS ]