1239460-75-3|5-Bromo-8-(trifluoromethyl)quinoline| Ambeed

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Quality Control of [ 1239460-75-3 ] Purity: 97% SDS Specification

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Product Details of [ 1239460-75-3 ]

CAS No. :	1239460-75-3
Formula :	C₁₀H₅BrF₃N
M.W :	276.05
SMILES Code :	FC(C1=C2N=CC=CC2=C(Br)C=C1)(F)F
MDL No. :	MFCD25542357
InChI Key :	NDIXNUDOSIZUCO-UHFFFAOYSA-N
Pubchem ID :	68754974

Safety of [ 1239460-75-3 ]

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

Computational Chemistry of [ 1239460-75-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	54.45
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.31
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.	5.17
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.	3.53
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	4.07
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.65

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.99
Solubility	0.0283 mg/ml ; 0.000103 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.	-3.13
Solubility	0.204 mg/ml ; 0.000738 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	-5.44
Solubility	0.00101 mg/ml ; 0.00000365 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.	-5.72 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	1.0
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)	1.66

Application In Synthesis of [ 1239460-75-3 ]

* 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.

Upstream synthesis route of [ 1239460-75-3 ]
Downstream synthetic route of [ 1239460-75-3 ]

[ 1239460-75-3 ] Synthesis Path-Upstream 1~1

1
[ 703-91-3 ]
[ 56-81-5 ]
[ 1239460-75-3 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: at 120℃; for 4 h; Stage #2: With water; sodium hydroxide In ethanol; ethyl acetate; nitrobenzene at 20℃;	To a mixture of 5-bromo-2-(trifluoromethyl)aniline (3.0g, 12.6mmol), glycerol (4.64g, 50.0mmol), and ferrous sulfate (0.56 g, 2.0mmol) was added cone, sulfuric acid (2.2mL) dropwise. The reaction mixture was heated at 120 ⁰C for 4hr. After cooled to RT, the reaction was diluted with ethyl acetate (15OmL), and 2N aq. NaOH was introduced to adjust pH about 13. The organic layer was separated and washed with brine and dried over Na₂SO₄ and evaporated to give the crude product, which was purified with flash column chromatography to give 5-bromo- 8-(trifluoromethyl)quinoline (1.2g, 48percent).

References: [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 101.
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5521 - 5527.

[ 1239460-75-3 ] Synthesis Path-Downstream 1~22

1
[ 703-91-3 ]
[ 56-81-5 ]
[ 1239460-75-3 ]

Yield	Reaction Conditions	Operation in experiment
48%		To a mixture of 5-bromo-2-(trifluoromethyl)aniline (3.0g, 12.6mmol), glycerol (4.64g, 50.0mmol), and ferrous sulfate (0.56 g, 2.0mmol) was added cone, sulfuric acid (2.2mL) dropwise. The reaction mixture was heated at 120 0C for 4hr. After cooled to RT, the reaction was diluted with ethyl acetate (15OmL), and 2N aq. NaOH was introduced to adjust pH about 13. The organic layer was separated and washed with brine and dried over Na2SO4 and evaporated to give the crude product, which was purified with flash column chromatography to give 5-bromo- 8-(trifluoromethyl)quinoline (1.2g, 48%).

References: [1]Patent: WO2010/91310,2010,A1 .Location in patent: Page/Page column 101.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5521 - 5527.

2
[ 1239460-75-3 ]
[ 1239460-74-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5521 - 5527.

3
[ 1239460-75-3 ]
[ 51656-70-3 ]
[ 1239460-76-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5521 - 5527.

4
[ 1239460-75-3 ]
[ 1270019-92-5 ]
tert-butyl N-[(3R,5S)-5-methyl-1-[8-(trifluoromethyl)quinolin-5-yl]piperidin-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; DavePhos; In N,N-dimethyl-formamide; at 130℃; for 3.0h;	At room temperature, to a solution of <strong>[1239460-75-3]5-bromo-8-(trifluoromethyl)quinoline</strong> (950mg, 3.44 minol) in DMF (10 mL) was added tert-butyl N-[(3R,5S)-5-methylpiperidin-3- yljcarbamate (718 mg, 3.35 mol), K3P04 (2.19 g, 10.29 minol), Pd2(dba)3CHC13 (356 mg, 0.34 minol) and DavePhos (270 mg, 0.69 minol). The resultingminxture was heated to 130 C and stirred for 3 h. After cooling to room temperature, the reactionminxture was diluted with water (10 mL). The resultingminxture was extracted with ethyl acetate (20 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 14% gradient) to yield tert-butyl N- [(3R,5S )-5-methyl- 1- [8-(trifluoromethyl)quinolin-5- yljpiperidin-3-yljcarbamate as yellow solid (1.10 g, 77%). MS: m/z = 410.2 [M+Hj.

References: [1]Patent: WO2017/106607,2017,A1 .Location in patent: Paragraph 00456; 00457.

5
[ 1239460-75-3 ]
[ 127199-55-7 ]
tert-butyl N-[(3R,4R)-4-methyl-1-[8-(trifluoromethyl)quinolin-5-yl]pyrrolidin-3-yl]carbamate [ No CAS ]