103862-55-1|5-Bromo-8-methoxy-2-methylquinoline| Ambeed

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Quality Control of [ 103862-55-1 ] Purity: 98% SDS Specification

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Product Details of [ 103862-55-1 ]

CAS No. :	103862-55-1
Formula :	C₁₁H₁₀BrNO
M.W :	252.11
SMILES Code :	CC1=NC2=C(OC)C=CC(Br)=C2C=C1
MDL No. :	MFCD04966993
InChI Key :	MCBRCJBMVOOJFX-UHFFFAOYSA-N
Pubchem ID :	4715021

Safety of [ 103862-55-1 ]

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

Computational Chemistry of [ 103862-55-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	10
Fraction Csp3	0.18
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	60.9
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.5
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	3.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.31
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.	2.47
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	3.56
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.91
Solubility	0.0308 mg/ml ; 0.000122 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.	-3.39
Solubility	0.103 mg/ml ; 0.000409 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	-5.07
Solubility	0.00214 mg/ml ; 0.00000847 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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.	-5.53 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<0.0
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)	1.82

Application In Synthesis of [ 103862-55-1 ]

* 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 [ 103862-55-1 ]

[ 103862-55-1 ] Synthesis Path-Downstream 1~30

1
[ 3033-80-5 ]
[ 103862-55-1 ]

Yield	Reaction Conditions	Operation in experiment
		5-Bromo-8-methoxy-2-methylquinoline 8-Methoxy-2-methylquinoline (7.92 g) was dissolved in methanol (80 mL), and bromine (2.37 mL) was added dropwise thereto under ice cooling, followed by stirring at room temperature for 1.5 hours. To the reaction liquid was added a saturated aqueous sodium thiosulfate solution and further added a saturated aqueous sodium hydrogen carbonate solution, followed by evaporating methanol under reduced pressure. This aqueous solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in this order, and then dried over anhydrous sodium sulfate. After evaporating the solvent, the desired product (47.6 g) was obtained as a yellow powder. 1H NMR (CDCl3, 400 MHz): delta 2.83 (3H, s), 4.07 (3H, s), 6.92 (1H, d, J=8.6 Hz), 7.42 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=8.6 Hz), 8.38 (1H, d, J=8.6 Hz).
		5-Bromo-8-methoxy-2-methylquinoline Commercially available 8-methoxy-2-methylquinoline (7.92 g) was dissolved in methanol (80 mL), and bromine (2.37 mL) was added dropwise thereto under ice cooling, followed by stirring at room temperature for 1.5 hours. To the reaction liquid was added a saturated aqueous sodium thiosulfate solution and further added a saturated aqueous sodium hydrogen carbonate solution, followed by evaporating methanol under reduced pressure. This aqueous solution was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the desired product (47.6 g) as a yellow powder. 1H-NMR (CDCl3, 400 MHz): delta 2.83 (3H, s), 4.07 (3H, s), 6.92 (1H, d, J=8.6 Hz), 7.42 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=8.6 Hz), 8.38 (1H, d, J=8.6 Hz).

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 1222 - 1226.
[2]Organic Letters,2001,vol. 3,p. 445 - 447.
[3]Dalton Transactions,2011,vol. 40,p. 5549 - 5556.
[4]Journal of the Chemical Society,1957,p. 290,293.
[5]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1617 - 1619.
[6]Patent: EP2168959,2010,A1 .Location in patent: Page/Page column 77.
[7]Patent: EP2168960,2010,A1 .Location in patent: Page/Page column 57.

2
[ 103862-55-1 ]
[ 24263-94-3 ]

References: [1]Journal of the Chemical Society,1957,p. 290,293.

3
[ 103862-55-1 ]
[ 103646-07-7 ]

References: [1]Journal of the Chemical Society,1957,p. 290,293.

4
[ 103862-55-1 ]
[ 201230-82-2 ]
8-methoxy-2-methyl-quinoline-5-carboxylic acid [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1617 - 1619.

5
[ 103862-55-1 ]
[ 4151-80-8 ]
[ 910231-06-0 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 6485 - 6496.

6
[ 90-04-0 ]
[ 103862-55-1 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 1222 - 1226.

7
[ 826-81-3 ]
[ 103862-55-1 ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1617 - 1619.

8
[ 103862-55-1 ]
[ 10522-47-1 ]

References: [1]Journal of the Chemical Society,1957,p. 290,293.

9
[ 103862-55-1 ]
[ 15599-52-7 ]

References: [1]Journal of the Chemical Society,1957,p. 290,293.

10
[ 103862-55-1 ]
[ 103859-96-7 ]

References: [1]Journal of the Chemical Society,1957,p. 290,293.

11
[ 108-30-5 ]
[ 103862-55-1 ]
[ 1005476-19-6 ]

Yield	Reaction Conditions	Operation in experiment
		4-(8-Methoxy-2-methylquinolin-5-yl)-4-oxobutyric acid The compound of Example 16 (7.24 g) was dissolved in THF (290 mL) under an argon gas atmosphere, and an n-butyl lithium/hexane solution (1.58 mol/L, 20.1 mL) was added dropwise thereto at -78C, followed by stirring at the same temperature for 5 minutes. Thereafter, a succinic anhydride (4.33 g)/THF (92 mL) solution was added thereto at -78C, followed by stirring at -78C for 30 minutes. To the reaction liquid was added a saturated aqueous ammonium chloride solution, followed by making the liquid property alkaline (pH 11) with the addition of a 10% aqueous sodium hydroxide solution and extraction with a 5% aqueous sodium hydroxide solution. The liquid property of the obtained aqueous layer was made acidic (pH 4) by the addition of concentrated hydrochloric acid, and the precipitate was collected by filtration to obtain the desired product (2.65 g) as a yellow powder. 1H NMR (CDCl3, 400 MHz): delta 2.79 (3H, s), 2.86 (2H, t, J=6.8 Hz), 3.40 (2H, t, J=6.8 Hz), 4.14 (3H, s), 7.02 (1H, d, J=8.6 Hz), 7.44 (1H, d, J=9.2 Hz), 8.11 (1H, d, J=8.6 Hz), 9.27 (1H, d, J=9.2 Hz).

References: [1]Patent: EP2168959,2010,A1 .Location in patent: Page/Page column 102.

12
[ 103862-55-1 ]
[ 123-62-6 ]
[ 1005475-81-9 ]

Yield	Reaction Conditions	Operation in experiment
		8-Methoxy-2-methyl-5-propionylquinoline The compound of Example 16 (5.55 g) was dissolved in THF (220 mL) under an argon gas atmosphere, and an n-butyl lithium/hexane solution (1.58 mol/L, 15.3 mL) was added dropwise thereto at -78C, followed by stirring at the same temperature for 5 minutes. Thereafter, propionic anhydride (4.86 mL) was added thereto at -78C, followed by stirring at -78C for 10 minutes. To the reaction liquid was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was then purified by silica gel column chromatography (hexane:ethyl acetate= 1:1?1:2) to obtain the desired product (2.39 g) as a yellow powder. 1H NMR (CDCl3, 400 MHz): delta 1.27 (3H, t, J=7.3 Hz), 2.80 (3H, s), 3.08 (2H, q, J=7.3 Hz), 4.14 (3H, s), 7.01 (1H, d, J=8.6 Hz), 7.44 (1H, d, J=9.2 Hz), 8.04 (1H, d, J=8.6 Hz), 9.26 (1H, d, J=9.2 Hz).

References: [1]Patent: EP2168959,2010,A1 .Location in patent: Page/Page column 92.

13
[ 103862-55-1 ]
[ 51608-60-7 ]
[ 1299463-28-7 ]

References: [1]Organic Letters,2011,vol. 13,p. 2580 - 2583.

14
[ 103862-55-1 ]
[ 1028353-74-3 ]

References: [1]Dalton Transactions,2011,vol. 40,p. 5549 - 5556.

15
[ 103862-55-1 ]
[ 423755-61-7 ]

References: [1]Dalton Transactions,2011,vol. 40,p. 5549 - 5556.

16
[ 103862-55-1 ]
[ 28611-39-4 ]
C₁₉H₂₀N₂O [ No CAS ]

References: [1]Dalton Transactions,2011,vol. 40,p. 5549 - 5556.

17
[ 103862-55-1 ]
[ 98-80-6 ]
2-methyl-5-phenyl-8-methoxylquinoline [ No CAS ]