886373-00-8|5-Bromo-2-ethoxypyridin-3-amine| Ambeed

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Quality Control of [ 886373-00-8 ] Purity: 97% SDS Specification

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Product Details of [ 886373-00-8 ]

CAS No. :	886373-00-8
Formula :	C₇H₉BrN₂O
M.W :	217.06
SMILES Code :	NC1=CC(Br)=CN=C1OCC
MDL No. :	MFCD07375021
InChI Key :	IQPXDUNQMPRRCP-UHFFFAOYSA-N
Pubchem ID :	53211699

Safety of [ 886373-00-8 ]

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

Computational Chemistry of [ 886373-00-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	47.64
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.11
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	1.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.83
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.	1.04
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	1.61
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.	-2.42
Solubility	0.823 mg/ml ; 0.00379 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.	-2.15
Solubility	1.54 mg/ml ; 0.00708 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	-3.06
Solubility	0.19 mg/ml ; 0.000875 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.	-6.54 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	0.0 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)	2.06

Application In Synthesis of [ 886373-00-8 ]

* 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 [ 886373-00-8 ]

[ 886373-00-8 ] Synthesis Path-Downstream 1~32

1
[ 886373-00-8 ]
[ 98-09-9 ]
[ 1086063-48-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridine; dmap; at 20℃; for 1h;Inert atmosphere;	Nu,Nu dimethylaminopyridine (15.7 mg, 0.128 mmol) and 5-bromo-2-(ethyloxy)-3- pyridinamine (reference: WO2009/147187, 278mg, 1.26 mmol) were combined with dry pyridine (3.94 ml_), before the addition of benzenesulfonyl chloride (0.16 ml_, 1.26 mmol) The resulting mixture was stirred at room temperature under nitrogen. After 1 hour the residue was concentrated, diluted with EtOAc, washed with water two times, then saturated NaHC03 followed by brine, dried (Na2S04) filtered and concentrated. The residue was purified by silica gel chromatography (0-60% EtOAc in hexanes). Fractions containing the product were combined and concentrated to yield N-[5-bromo-2-(ethyloxy)-3-pyridinyl]benzenesulfonamide (322 mg, 65%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 10.12 (s, 1 H) 8.03 (d, J=2.1 Hz, 1 H) 7.77 - 7.69 (m, 3 H) 7.68- 7.62 (m, 1 H) 7.60 - 7.52 (m, 2 H) 4.04 (q, J=7.0 Hz, 2 H) 1.06 (t, J=7.0 Hz, 3 H).
	With pyridine; at 20℃; for 20h;	Intermediate 61 lambda/-[5-Bromo-2-(ethyloxy)-3-pyridinyl]benzenesulfonamide A solution of <strong>[886373-00-8]5-bromo-2-(ethyloxy)-3-pyridinamine</strong> (1.45 g) in anhydrous pyridine (15 ml) was treated with benzenesulfonyl chloride (1.03 ml) then stirred at RT for 20 hr. The reaction was evaporated to dryness and the residue was purified by column chromatography on silica, eluting with 30% hexanes in DCM, to give the title compound (1.86 g).1H NMR: deltaH (DMSOd6, 400 MHz) 10.09 (1 H, s), 8.03 (1 H, d), 7.74 (1 H, d), 7.71 (1 H, d), 7.64 (1 H, d), 7.57 (2H, d), 4.05 (2H, q), 1.07 (3H, t).

References: [1]Patent: WO2012/37108,2012,A1 .Location in patent: Page/Page column 238.
[2]Patent: WO2009/147187,2009,A1 .Location in patent: Page/Page column 132.

2
[ 886372-76-5 ]
[ 886373-00-8 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a solution of 5-bromo-2-ethoxy-3-nitropyridine (75.2 mg, 0.304 mmol) in ethyl acetate (3 mL) was added tin(II) chloride (289 mg, 1.52 mmol), and the mixture was heated to reflux for 2 h. After cooling to rt, 50% aqueous sodium hydroxide was added dropwise until a sticky brown solid completely formed. Sodium sulfate was then added, and the mixture was stirred for several minutes. The solids were then removed by filtration. The filtrate was dried over sodium sulfate, filtered, and concentrated in vacuo to provide 5-bromo-2-ethoxypyridin-3-amine (53 mg, 0.25 mmol, 80% yield) as a dark blue film. 1H NMR (400 MHz, CDCl3) delta 7.56 (d, 1H), 6.97 (d, 1H), 4.37 (q, 2H), 3.85 (br s, 2H), 1.40 (dd, 3H); MS (EI) for C7H9BrN2O: 217, 219 (Br isotopes, MH+).
79%	With ammonium chloride; zinc; In methanol; dichloromethane; at 75℃; for 4h;	j00144] Step 2: To a stirred solution of 5.bromo.-2-ethoxy3-nitTopyridine (1.0 equiv.) in MeOH and DCM (10:1, 0.27 M) at 25 C were added zinc (5.5 equiv.) and ammonium chloride (5.0 equiv.) and the mixture was heated to 75 C and stirred for 4 h. LCMS shows complete consumption of starting material and fairly clean conversion to a desired product (M±I=217/219, R=O.75). The reaction was cooled to room temp and filtered through a short plug of Celite, washing with DCM, and then concentrated to remove MeOH. The residue was taken up in EtOAc, washed with water and brine and then dried (MgSO1) and concentrated.The residue was quickly passed through a silica column. eluting with 0-50% EtOAc:heptanc. Product clutes around 20% EtOAc and was concentrated to give 5-bromo-2- ethoxypyridin-3-amine in 79 % yield as a light brown solid. LCMS (th) (M+H) = 217/219, Rt = 0.75 mm.
		Intermediate 62 5-Bromo-2-(ethyloxy)-3-pyridinamine A solution of 5-bromo-2-(ethyloxy)-3-nitropyridine (15.5 g) in EtOAc (300 ml) was treated with tin(ll) chloride anhydrate (56.6 g) then heated at reflux for 2.5 hr. The reaction was cooled to RT then evaporated to dryness. The residue was treated with 2M NaOH (aq) (500 ml) that was treated with anhydrous magnesium sulfate (~ 50 g) then slurried to give a filterable sludge. The filtrate was separated and the organic phase was washed with brine, dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica, eluting with DCM, to give the title compound. 1H NMR: deltaH (DMSO-d6, 400 MHz) 7.37 (1 H, d), 6.98 (1 H, d), 5.24 (2H, br.s.), 4.27 (2H, q), 1.31 (3H, t).

References: [1]Patent: WO2010/135524,2010,A1 .Location in patent: Page/Page column 237.
[2]Patent: WO2016/38582,2016,A1 .Location in patent: Paragraph 00144.
[3]Patent: WO2009/147187,2009,A1 .Location in patent: Page/Page column 132.

3
[ 886373-00-8 ]
[ 124-63-0 ]
[ 1256957-66-0 ]

Yield	Reaction Conditions	Operation in experiment
43%		A solution of <strong>[886373-00-8]5-bromo-2-ethoxypyridin-3-amine</strong> (53 mg, 0.25 mmol) and diisopropylethylamine (96 uL, 0.55 mmol) in dichloromethane (1 mL) was cooled to 0 C and methanesulfonyl chloride (39 uL, 0.5 mmol) was added. The mixture was allowed to warm to rt over 15 h, and then water was added. The resulting mixture was extracted with dichloromethane. The organic extract was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in methanol (500 uL) and dioxane (500 uL), and then sodium hydroxide (2 M, 190 uL, 0.38 mmol) was added. The mixture was heated to 60 C and 3 drops of aqueous sodium hydroxide (50%) were added. After stirring a further 30 min, the mixture was cooled to rt. Dilution with water was followed by acidification with aqueous citric acid (10%) and then two extractions with ethyl acetate. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (gradient 100% hexanes to 70% hexanes : 30% ethyl acetate) to provide N-(5-bromo-2-ethoxypyridin-3- yl)methanesulfonamide (32.1 mg, 0.11 mmol, 43% yield) as a colorless film. 1H NMR (400 MHz, CDCl3) delta 7.95 (d, 1H), 7.89 (d, 1H), 6.75 (br s, 1H), 4.42 (q, 2H), 3.05 (s, 3H), 1.41 (t, 3H); MS (EI) for C8HnBrN2O3S: 295, 297 (Br isotopes, MH+).

References: [1]Patent: WO2010/135524,2010,A1 .Location in patent: Page/Page column 237-238.

4
[ 886373-00-8 ]
[ 1366129-92-1 ]

References: [1]Patent: WO2012/37108,2012,A1 .

5
[ 886373-00-8 ]
[ 1366131-84-1 ]

References: [1]Patent: WO2012/37108,2012,A1 .

6
[ 67443-38-3 ]
[ 886373-00-8 ]

References: [1]Patent: WO2016/38582,2016,A1 .
[2]Patent: WO2009/147187,2009,A1 .

7
[ 886373-00-8 ]
5-bromo-2-ethoxy-3-iodopyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		j00145] Step 3: To a stirred solution of 5-bromo-2-ethoxyp ridin-3-amine (1.0 equw.) in cone. HCI and Water (1:1.35, 0.07 M) at 0 C was slowly added NaNO2 (1.1 equiv.) and the mixture was stimed for 30 mm. A solution of KI (3.0 equiv.) in Water (0.07 M) was slowly added to the mixture, which was then allowed to warm to 25 C and stirred fo:r 30 mm. The mixture was poured into a separatory funnel and extracted with EtOAc (3 X). LCMS of the organic extracts shows mostly desired product (M÷i=327/3 29, R1=i ii) with a small amount of unreacted starting material. The combined organics were washed with sat. aq. Na2SO3 and sat. aq. Na2CO3 and then dried (MgSO4) and concentrated. The residue was purified via Grace flash column chromatography (0-15% EtOAc:heptane). Product co-elutes with the unreacted starting material and was concentrated to give 5-bromo-2-ethoxy-3- iodopyridine in 95 % yield as a dark orange oil. LCMS Qn/z) (M÷H) = 327/329, Rt = 111 inln.

References: [1]Patent: WO2016/38582,2016,A1 .Location in patent: Paragraph 00145.

8
[ 886373-00-8 ]
3-(6-ethoxy-5-(3-methyloxetan-3-yl)pyridin-3-yl)-4-methylaniline [ No CAS ]