1479-58-9|(2-Amino-5-bromophenyl)(2-fluorophenyl)methanone| Ambeed

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Quality Control of [ 1479-58-9 ] Purity: 97% SDS Specification

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Product Details of [ 1479-58-9 ]

CAS No. :	1479-58-9
Formula :	C₁₃H₉BrFNO
M.W :	294.12
SMILES Code :	O=C(C1=CC=CC=C1F)C2=CC(Br)=CC=C2N
MDL No. :	MFCD00038380
InChI Key :	XCOKDXNGCQXFCV-UHFFFAOYSA-N
Pubchem ID :	73865

Safety of [ 1479-58-9 ]

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

Computational Chemistry of [ 1479-58-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	68.38
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.26
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	3.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.83
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.	3.39
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	3.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.43

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.53
Solubility	0.00868 mg/ml ; 0.0000295 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.53
Solubility	0.0086 mg/ml ; 0.0000292 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-5.63
Solubility	0.000694 mg/ml ; 0.00000236 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	Yes
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.	-5.3 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.	1.0 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)	2.09

Application In Synthesis of [ 1479-58-9 ]

* 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 [ 1479-58-9 ]

[ 1479-58-9 ] Synthesis Path-Downstream 1~33

2
[ 1479-58-9 ]
[ 598-21-0 ]
[ 2647-50-9 ]

References: [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 30.
[2]Patent: WO2003/82832,2003,A2 .Location in patent: Page/Page column 42.

3
[ 15761-38-3 ]
[ 1479-58-9 ]
(S)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h;	{1-[4-Bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 116.; To a stirred solution of <strong>[1479-58-9](2-amino-5-bromophenyl)-(2-fluoro-phenyl)-methanone</strong> (60 g, 204 mmol) 115 and the N-Boc-L-alanine 107 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid residue 116 was purified by recrystallization from hexane and EtOAc to afford 116 (74.9 g, 79percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=-59.1 (c 0.51, EtOAc).

References: [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 58-59.

4
[ 3744-87-4 ]
[ 1479-58-9 ]
(R)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h;	{1-[4-Bromo-2-(2-fluorobenzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 136; To a stirred solution of (2-amino-5-bromophenyl)-(2'-fluoro-phenyl)-methanone 115 (60 g, 204 mmol) and the N-Boc-D-alanine 129 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid product 136 was purified by recrystallization from hexane and EtoAc to afford 136 (73 g, 77percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=59.6 (c 0.51, EtOAc).

References: [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 65-66.

5
[ 1479-58-9 ]
[ 103321-49-9 ]
[ 885124-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; for 2.0h;Heating / reflux;	Example 1, Step 1 : fluorophenyl)carbo A round-bottomed flask was charged with (2-amino-5-bromophenyl)(2- fluorophenyl)methanone (1.45g), 9/-/-fluoren-9-ylmethyl (2-chloro-2- oxoethyl)carbamate (1.6g) and chloroform (15OmL). The mixture was heated to reflux for 2h then concentrated to dryness. The residue was taken up in a mixture of EPO <DP n="26"/>a saturated solution of sodium bicarbonate and ethyl acetate. The resulting solids were collected on a filter and washed first with water then with diethyl ether. Thorough air-drying provided 9/-/-fluoren-9-ylmethyl [2-({4-bromo>-2-[(2- fluorophenyl)carbonyl] phenyl}amino)-2-oxoethyl]carbamate (2g) as a light yellow powder. H1 NMR (d6-dmso): 10.8 (br s, 1 H), 7.95 (d, 1 H), 7.75-7.90 (m, 4H), 7.45- 7.70 (m, 5H), 7.20-7.42 (m, 6H), 4.30 (d, 2H), 4.20 (t, 1 H), 3.65 (d, 2H).

References: [1]Patent: WO2006/44753,2006,A2 .Location in patent: Page/Page column 24-25.

6
[ 1479-58-9 ]
5'Bromo-2-(3,4-dimethoxyphenylsulfonamido)-2'-fluorobenzophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;3,4-dimethoxybenzene-1-sulfonyl chloride; In pyridine; water;	B) 5'Bromo-2-(3,4-dimethoxyphenylsulfonamido)-2'-fluorobenzophenone. 20 g of <strong>[1479-58-9]2-amino-5-bromo-2'-fluorobenzophenone</strong> are heated at 85° C. for 48 hours in 120 ml of dry pyridine in the presence of 20 g of 3,4-dimethoxyphenylsulfonyl chloride. The mixture is cooled, poured into ice-cold water, the solid is filtered off, the solid is extracted with AcOEt, the organic phase is washed with water, a solution of hydrochloric acid (1N), water and then saline water. After drying over magnesium sulfate and evaporating the solvent under vacuum, a solid is obtained which is recrystallized from DCM/isopropyl ether. m=28 g M.p.=125°-128° C.

References: [1]Patent: US5338755,1994,A .

7
[ 124612-15-3 ]
[ 1479-58-9 ]
[ 1052719-57-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4172 - 4176.

8
[ 1479-58-9 ]
[ 598-21-0 ]
[ 1647-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In chloroform; at 0℃; for 2.0h;	Example 34 Step 1.2-Bromo-N-(4-bromo-2-(2-fluorobenzoyl)phenyl)acetamide.; A mixture of <strong>[1479-58-9](2-amino-5-bromophenyl)(2-fluorophenyl)methanone</strong> (15 g, 51.0 mmol) and sodium bicarbonate (12.85 g, 153 mmol) in CHCl3 (150 mL) was cooled in an ice bath to 0° C. A solution of 2-bromoacetyl bromide (4.89 mL, 56.1 mmol) was added drop-wise slowly and washed in with CHCl3 (30 ml). The cooling was removed and the mixture was stirred for 2 hr.The reaction mixture was washed with aqueous NaHCO3 (5percent) and dried with brine. The CHCl3 was removed in vacuo and the residue was stirred with. The solid product was filtered, washed with ether and air dried to a yellow powder. The material was taken on without purification.

References: [1]Patent: US2009/93466,2009,A1 .Location in patent: Page/Page column 12-13.

9
[ 1479-58-9 ]
[ 70577-95-6 ]
methyl 6-bromo-4-(2-fluorophenyl)-2-(trifluoromethyl)quinoline-3-carboxylate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2013,p. 8323 - 8329.

10
[ 1479-58-9 ]
[ 70577-95-6 ]
C₁₈H₁₂BrF₄NO₃ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2013,p. 8323 - 8329.

11
[ 1479-58-9 ]
[ 108-94-1 ]
2-bromo-9-(2-fluorophenyl)acridine [ No CAS ]

References: [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 577 - 581.

12
[ 1479-58-9 ]
6-bromo-4-(2-fluorophenyl)cinnoline [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6318 - 6322.

13
[ 1479-58-9 ]
[ 1779-49-3 ]
4-bromo-2-(1-(2-fluorophenyl)vinyl)aniline [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 1534 - 1537.
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6318 - 6322.
[3]Journal of Organic Chemistry,2017,vol. 82,p. 10110 - 10120.

14
[ 3744-87-4 ]
[ 1479-58-9 ]
(R)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Patent: WO2017/161370,2017,A1 .Location in patent: Paragraph 00158.

15
[ 15761-38-3 ]
[ 1479-58-9 ]
(S)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Patent: WO2017/161370,2017,A1 .Location in patent: Paragraph 00158.

16
[ 1479-58-9 ]
[ 872873-97-7 ]