109613-97-0|2-Bromo-4-methoxypyridin-3-amine| Ambeed

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Quality Control of [ 109613-97-0 ] Purity: 97% SDS Specification

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Product Details of [ 109613-97-0 ]

CAS No. :	109613-97-0
Formula :	C₆H₇BrN₂O
M.W :	203.04
SMILES Code :	NC1=C(OC)C=CN=C1Br
MDL No. :	MFCD11044243
InChI Key :	JAABPGVJVYZBDJ-UHFFFAOYSA-N
Pubchem ID :	13873118

Safety of [ 109613-97-0 ]

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

Computational Chemistry of [ 109613-97-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	42.83
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.	1.69
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	1.17
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.44
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.	0.31
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	1.31
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.21
Solubility	1.24 mg/ml ; 0.00611 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.	-1.78
Solubility	3.4 mg/ml ; 0.0167 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	-2.65
Solubility	0.453 mg/ml ; 0.00223 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	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.	-6.71 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	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)	1.97

Application In Synthesis of [ 109613-97-0 ]

* 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 [ 109613-97-0 ]

[ 109613-97-0 ] Synthesis Path-Downstream 1~22

1
[ 33631-09-3 ]
[ 109613-97-0 ]

Yield	Reaction Conditions	Operation in experiment
82%		To a solution of 4-methoxy-pyridin-3-ylamine (6.76 g, 54.5 mmol) in cone. HC1 (50 mL) is added Br2 (3.36 mL, 65.4 mmol) dropwise over a 30 s period. This mixture is stirred at rt for 1 h,and then heated at 55 C overnight. The mixture is cooled to rt, and then poured into ice. Cone. NH4OH is added until the pH of the solution is basic. The resulting suspension is partitioned between H20 and EtOAc. The two layers are separated, and the aqueous layer is extracted with EtOAc (2X). The combined organic layers are washed with H20 and brine, dried over MgS04, filtered, and concentrated in vacuo. The crude material is purified on silica gelwith EtOAc/MeOH (lOO/o to 80/20) as elant to yield 9.18 g (82%) of the product as a white powder. 1H NMR (CDC13, 300 MHz) 7.75 (d, J= 5.3, 1H), 6.68 (d, J(br s, 2H), 3.91 (s, 3H). LC Rt: 0.89 min; LCMS m/z 203 (M+l, 100%).
77%	With N-Bromosuccinimide; trifluoroacetic acid; at 20℃;	The solution of 4-methoxypyridin-3-amine (3.1 g, 24.97 mmol) in TFA (38.5 ml, 499 mmol) was stirred at ice bath temperature and to the mixture was added NBS (4.89 g, 27.5 mmol) in several batches. The reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated in vacuo and the residue was diluted with saturated NaHCO3 solution and ethyl acetate. The organic layers (twice extracts) were combined and washed with saturated NaHCO3 solution, dried over MgSO4. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography. The product was eluted with 0-20% ethyl acetate in hexane to give the desired product as a white solid (3.9 g, 77%); HPLC: RT=0.47 min (H2O/ACN with 0.05% TFA, Waters Acquity SDS C18, 2.1×50 mm, 1.7-mum particles, gradient=1.8 min, wavelength=220 nm); MS (ES): m/z=202.8, 204.8 [M+H]+; 1H NMR (400 MHz, CDCl3) delta ppm 7.75 (d, J=5.5 Hz, 1H), 6.69 (d, J=5.5 Hz, 1H), 4.11 (d, J=6.2 Hz, 2H), 3.92 (s, 3H).
2.74 g	With hydrogenchloride; bromine; In water; at 20 - 55℃;	To a solution of 4-methoxypyridin-3-amine (purchased from Ark Pharm Inc.), (3 g) in concentrated HCl (22.17 mL) was added bromine (1.49 mL) dropwise over a 30 s period and the mixture stirred at rt for 1 h and then at 55 C. over the weekend. The reaction mixture was allowed to cool to rt and then poured into ice (250 g). Concentrated NH4OH was added until the pH of the solution was basic (pH ?9). The resulting solution was then partitioned between H2O and EtOAc and the two layers separated. The aqueous layer was extracted with EtOAc (2*) and the combined organic layers washed with water and brine, dried (MgSO4), filtered and evaporated under vacuum to give a solid which was dissolved in DCM and purified by column chromatography (normal phase, 100 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 0-20% EtOAc in n-hexane) to give the desired product (2.74 g). LCMS: m/z 203.37 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 3.93 (s, 3H) 3.95-4.60 (br. s., 2H) 6.69 (d, J=5.4 Hz, 1H) 7.76 (d, J=5.3 Hz, 1H)

2.74 g

With hydrogenchloride; bromine; In water; at 20 - 55℃;

To a solution of 4-methoxypyridin-3-amine (purchased from Ark Pharm Inc.), (3 g) in concentrated HCl (22.17 mL) was added bromine (1.49 mL) dropwise over a 30 s period and the mixture stirred at rt for 1 h and then at 55 C. over the weekend. The reaction mixture was allowed to cool to rt and then poured into ice (250 g). Concentrated NH4OH was added until the pH of the solution was basic (pH ?9). The resulting solution was then partitioned between H2O and EtOAc and the two layers separated. The aqueous layer was extracted with EtOAc (2*) and the combined organic layers washed with water and brine, dried (MgSO4), filtered and evaporated under vacuum to give a solid which was dissolved in DCM and purified by column chromatography (normal phase, 100 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 0-20% EtOAc in n-hexane) to give the desired product (2.74 g). LCMS: m/z 203.37 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 3.93 (s, 3H) 3.95-4.60 (br. s., 2H) 6.69 (d, J=5.4 Hz, 1H) 7.76 (d, J=5.3 Hz, 1H)

References: [1]Patent: WO2011/78984,2011,A1 .Location in patent: Page/Page column 62; 63.
[2]Liebigs Annalen der Chemie,1987,p. 857 - 862.
[3]Patent: US2016/176871,2016,A1 .Location in patent: Paragraph 0924-0925.
[4]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0450-0453.
[5]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 53; 54.

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[ 109613-97-0 ]
[ 109613-98-1 ]