99455-08-0|7-Bromo-2-methoxyquinoline| Ambeed

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Quality Control of [ 99455-08-0 ] Purity: 97% SDS Specification

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Product Details of [ 99455-08-0 ]

CAS No. :	99455-08-0
Formula :	C₁₀H₈BrNO
M.W :	238.08
SMILES Code :	COC1=NC2=CC(Br)=CC=C2C=C1
MDL No. :	MFCD11877930
InChI Key :	ARPAPTVOXJPIHY-UHFFFAOYSA-N
Pubchem ID :	14220970

Safety of [ 99455-08-0 ]

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

Computational Chemistry of [ 99455-08-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	55.94
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.	2.66
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	3.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.01
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.	2.6
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	3.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.91

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.83
Solubility	0.0353 mg/ml ; 0.000148 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.	-3.33
Solubility	0.112 mg/ml ; 0.000472 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	-4.69
Solubility	0.00489 mg/ml ; 0.0000206 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	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.	-5.49 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)	1.8

Application In Synthesis of [ 99455-08-0 ]

* 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 [ 99455-08-0 ]

[ 99455-08-0 ] Synthesis Path-Downstream 1~27

1
[ 626-55-1 ]
[ 99455-08-0 ]
[ 99455-34-2 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2048 - 2056.

2
[ 124-41-4 ]
[ 99455-15-9 ]
[ 99455-08-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	In methanol; for 16.0h;Reflux;	This compound was prepared from 7-bromo-2-chloroquinoline(2) in 98% yield as described for compound 1; Mp 68-69 C; 1HNMR (300 MHz, CDCl3): delta 8.05 (d, 1H, 1.8 Hz), 7.93 (d, 1H, 8.7 Hz),7.57 (d, 1H, 9.0 Hz), 7.47 (dd, 1H, 8.7 Hz and 1.8 Hz), 6.91 (d, 1H,9.0 Hz), 4.00 (s, 3H); MS (APCI, pos. 30 V) m/z: [M+H]+, 239.06.

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1657 - 1662.
[2]European Journal of Medicinal Chemistry,2017,vol. 127,p. 621 - 631.
[3]Journal of Medicinal Chemistry,1988,vol. 31,p. 2048 - 2056.

3
[ 99455-08-0 ]
[ 99470-99-2 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2048 - 2056.

4
[ 99465-10-8 ]
[ 99455-08-0 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2048 - 2056.

5
[ 99465-18-6 ]
[ 99455-08-0 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2048 - 2056.

6
[ 591-19-5 ]
[ 99455-08-0 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2048 - 2056.

7
[ 886853-93-6 ]
[ 99455-08-0 ]
[ 1223559-71-4 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1657 - 1662.

8
[ 1223559-74-7 ]
[ 99455-08-0 ]
[ 1223559-77-0 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1657 - 1662.

9
[ 177-11-7 ]
[ 99455-08-0 ]
8-(2-methoxy-7-quinolyl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
900 mg	With sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 12.0h;Inert atmosphere;	To a solution of 1,4-dioxa-8-azaspiro[4.5]decane (550 mg, 3.06 mmol) and 7-bromo-2- methoxyquinoline (875 mg, 3.67 mmol) in dioxane (5 mL) was added t-BuONa (883 mg, 9.18 mmol) under N2. After being heated with stirring at 100 C for 12 hrs, the resulting reaction mixture was cooled to rt and concentrated in vacuo. The residue was diluted with H20 (60 mL) and extracted with DCM (150 mL). The organic layer was washed with brine (60 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column to give 8- (2-methoxy-7 -quinolyl)- 1 ,4-dioxa-8-azaspiro [4.5] decane (900 mg) as yellow oil.

References: [1]Patent: WO2016/107832,2016,A1 .Location in patent: Page/Page column 130; 131.

10
[ 99455-08-0 ]
1-(2-methoxy-7-quinolyl)piperidin-4-one [ No CAS ]

References: [1]Patent: WO2016/107832,2016,A1 .

11
[ 99455-08-0 ]
6-(2-methoxy-7-quinolyl)-2-pyrimidin-2-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine [ No CAS ]

References: [1]Patent: WO2016/107832,2016,A1 .

12
[ 99455-08-0 ]
2-(2-methoxyquinolin-7-yl)ethanamine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 621 - 631.

13
[ 99455-08-0 ]
N-(2-(2-methoxyquinolin-7-yl)ethyl)acetamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 621 - 631.

14
[ 99455-08-0 ]
N-(2-(2-methoxyquinolin-7-yl)ethyl)isoindoline-1,3-dione [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 621 - 631.

15
[ 3485-84-5 ]
[ 99455-08-0 ]
(E)-N-(2-(2-methoxyquinolin-7-yl)vinyl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-d6-formamide; at 110.0℃; for 3.0h;Sealed tube; Inert atmosphere;	General procedure: In a sealed tube under argon atmosphere, were introducedcompound 4 (4.74 g, 20 mmol), DMF (20 mL), triethylamine(11.16 mL, 80 mmol), palladium diacetate (225 mg, 1 mmol), tri(otolyl)-phosphine (609 mg, 2 mmol) and N-vinylphthalimide (5.20 g,30 mmol). The mixturewas stirred at 110 C for 3 h and hydrolyzed.The formed solid was solubilized in CH2Cl2, washed with water andbrine, dried over MgSO4 and evaporated under reduced pressure.The crude productwas recrystallized from acetonitrile to afford 7 asa white solid (91% yield)

References: [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 621 - 631.

16
[ 99455-08-0 ]
[ 140-88-5 ]
(E)-ethyl 3-(2-methoxyquinolin-7-yl)prop-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In N,N-dimethyl-formamide; at 120.0℃; for 15.0h;Inert atmosphere;	General procedure: To a solution of 2 (30.63 g, 100 mmol) in DMF (150 mL) under an inert atmosphere, were added ethyl acrylate (11.97 mL, 110 mmol), bis(triphenylphosphine) palladium chloride (7.72 g, 11 mmol) and triethylamine (15.29 mL, 110 mmol). The reaction mixture was refluxed at 120 C for 15 h, cooled to room temperature, hydrolyzed with water and then extracted twice with ethyl acetate. The combined organic layers were washed with a 1 M solution of HCl, water and brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography (SiO2, cyclohexane/EtOAc: 7/3) to give 4 (77%) as a white solid.