2840-29-1|3-Amino-4-bromobenzoic acid| Ambeed

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Quality Control of [ 2840-29-1 ] Purity: 98% SDS Specification

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Product Details of [ 2840-29-1 ]

CAS No. :	2840-29-1
Formula :	C₇H₆BrNO₂
M.W :	216.03
SMILES Code :	O=C(O)C1=CC=C(Br)C(N)=C1
MDL No. :	MFCD00579106
InChI Key :	TZFJADFQEBASQU-UHFFFAOYSA-N
Pubchem ID :	3418752

Safety of [ 2840-29-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 2840-29-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	45.51
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.28
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	1.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.74
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.	0.64
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	1.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.27

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.46
Solubility	0.746 mg/ml ; 0.00345 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.	-2.44
Solubility	0.789 mg/ml ; 0.00365 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	-2.27
Solubility	1.16 mg/ml ; 0.00536 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.	-6.55 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.	0.56

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)	1.18

Application In Synthesis of [ 2840-29-1 ]

* 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 [ 2840-29-1 ]

[ 2840-29-1 ] Synthesis Path-Downstream 1~35

1
[ 6319-40-0 ]
[ 2840-29-1 ]

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 880 - 886.
[2]Patent: WO2006/51851,2006,A1 .Location in patent: Page/Page column 59.
[3]Justus Liebigs Annalen der Chemie,1884,vol. 222,p. 183.

2
[ 2840-29-1 ]
[ 619-03-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1884,vol. 222,p. 184.
[2]Recueil des Travaux Chimiques des Pays-Bas,1915,vol. 34,p. 162.

3
[ 2840-29-1 ]
[ 99-05-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1884,vol. 222,p. 183.

4
[ 2840-29-1 ]
[ 56-81-5 ]
[ 204782-96-7 ]

References: [1]Justus Liebigs Annalen der Chemie,1887,vol. 237,p. 323.
[2]Justus Liebigs Annalen der Chemie,1887,vol. 237,p. 323.

5
[ 7647-01-0 ]
[ 6319-40-0 ]
tin [ No CAS ]
[ 2840-29-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1884,vol. 222,p. 178 Anm. 1.

7
[ 2840-29-1 ]
copper cyanide [ No CAS ]
[ 887757-25-7 ]

References: [1]Chemische Berichte,1891,vol. 24,p. 3768.

8
[ 2840-29-1 ]
[ 6939-93-1 ]

References: [1]Chemische Berichte,1891,vol. 24,p. 3768.

9
[ 2840-29-1 ]
[ 56984-35-1 ]

References: [1]Chemische Berichte,1891,vol. 24,p. 3768.

10
nickel (II) chloride hexahydrate [ No CAS ]
[ 6319-40-0 ]
[ 2840-29-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium borohydrid; In methanol; ethyl acetate;	Reference Example 35 The compound in Reference Example 34 (4.94 g, 20.1 mmol) and nickel chloride-hexahydrate (9.56 g, 40.2 mmol) were mixed in methanol (100 mL) and the solution was stirred. Then, sodium borohydride (3.8 g, 0.1 mol) was added gradually, while the solution was cooled on an ice bath to keep the reaction temperature low. Then, the mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure; the residue was dissolved in ethyl acetate; the solution was filtered through Celite; and the filtrate was washed with saturated aqueous citric acid solution and then saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the precipitated crystals were washed with hexane, to obtain 3-amino-4-bromobenzoic acid (2.95 g, 68%) as a colorless solid. 1H-NMR(DYSO-d6),delta:7.01(1H,dd,J=8.3,2.5Hz),7.39 (1H, d, J = 2.5Hz), 7.45 (1H, d, J = 8.3Hz) ppm FABMS:215(M+1)

References: [1]Patent: EP1820799,2007,A1 .

11
[ 2840-29-1 ]
[ 1126745-42-3 ]

Yield	Reaction Conditions	Operation in experiment
48.9%	With thionyl chloride; In toluene; for 2h;Heating / reflux;	Thionyl chloride (4.4 g, 37 mmol) was added to a solution of 3-amino-4-bromo- benzoic acid (2 g, 9.25 mmol) in toluene (12 ml). The reaction mixture was heated to reflux for 2 hours. Excess thionyl chloride and toluene were distilled off under reduced pressure. The purification of the residue was performed by bulb-to-bulb distillation at 130C under vacuum (0.40 mbar) to give 3-sulfinylamino-4-bromo-benzoyl chloride (0.978 g, 48.9% yield).

References: [1]Patent: WO2009/30457,2009,A1 .Location in patent: Page/Page column 17.

12
[ 2840-29-1 ]
[ 557-21-1 ]
[ 159847-71-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 20 - 100℃; for 15h;	To a solution of <strong>[2840-29-1]3-amino-4-bromo-benzoic acid</strong> (6.0 g, 276 mmol) in dimethyl formamide (30 ml), was added sequentially at ambient temperature zinc cyanide (11.66 g, 99.4 mmol) and tetrakis(triphenylphosphine)palladium (9.57 g, 8.28 mmol). The mixture was heated to 100C for 14 hours. The reaction mixture was allowed to cool to <n="29"/>ambient temperature before the sequential addition of more zinc cyanide (0.65 g, 5.54 mmol) and tetrakis(triphenylphosphine)palladium (1.9 g, 1.64 mmol) at ambient temperature. The mixture was heated to 1000C for 1 more hour. The reaction mixture was allowed to cool to ambient temperature and was quenched by addition of a mixture of toluene and aqueous ammonia (IM). The phases were separated and the aqueous layer was extracted with toluene. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate / cyclohexane 1:2 to 1 :0) to give 3-amino-4-cyano-benzoic acid (2.94 g, 67% yield).

References: [1]Patent: WO2009/30457,2009,A1 .Location in patent: Page/Page column 26-27.

13
[ 2840-29-1 ]
[ 544-92-3 ]
[ 887757-25-7 ]

References: [1]Patent: WO2006/51851,2006,A1 .Location in patent: Page/Page column 61-62.

14
[ 2840-29-1 ]
[ 67-63-0 ]
[ 1249772-15-3 ]

References: [1]Organic Letters,2011,vol. 13,p. 2326 - 2329.

15
[ 2840-29-1 ]
[ 4559-70-0 ]
[ 1367551-68-5 ]

Yield	Reaction Conditions	Operation in experiment
41%	With palladium on activated charcoal; potassium carbonate; In water; at 180℃; for 1h;Microwave irradiation;	Standard conditions: iodobenzoic acid (0.55 mmol) , HP(0)Ph2, base, Pd/C, 0 (10 mL) , conventional heating, 100 C, 1 h. b 70 C.

References: [1]Organic Letters,2012,vol. 14,p. 2188 - 2190.
[2]Patent: WO2013/117440,2013,A1 .Location in patent: Page/Page column 8.

16
[ 655256-68-1 ]
[ 2840-29-1 ]
[ 1426531-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N1,N1-dimethyl-N2-((propylimino)methylene)ethane-1,2-diamine; benzotriazol-1-ol; In dichloromethane; for 24h;Inert atmosphere;	Step 1 : 3-Amino-4-bromo-N-(2-(4-methylpiperazin-1 -yl)benzyl)benzamideN1 ,N1-dimethyl-N2-((propylimino)methylene)ethane-1 ,2-diamine (0.70 ml, 3.99 mmol) was added to a stirred solution / suspension of <strong>[2840-29-1]3-amino-4-bromobenzoic acid</strong> (719 mg, 3.33 mmol), (2-(4-methylpiperazin-1-yl)phenyl)methanamine (820 mg, 3.99 mmol) and HOBt (140 mg, 1.0 mmol) in dry DCM (20 ml) under argon. After 24 hrs the reaction mixture was diluted with DCM and washed several times with water. The solvent was removed in vacuo and the resulting yellow oil was triturated with DCM/ diethyl to give a yellow crystalline powder;LCMS: Rt 0.85 min; MS m/z 403.2 [M+H]+; Method 2minl_C_v0031 H NMR (400 MHz, CDCI3) delta 6.48 (1 H, d), 6.42 (1 H, br s), 7.30 (3H, m), 7.20 (1 H, d), 7.14 (1 H, t), 6.92 (1 H, d), 4.72 (2H, d), 4.23 (2H, br s), 3.02 (4H, br s(, 2.62 (4H, br s), 2.35 (3H, s)

References: [1]Patent: WO2013/30802,2013,A1 .Location in patent: Page/Page column 94.

17
[ 655256-68-1 ]
[ 2840-29-1 ]
[ 1426531-14-7 ]

References: [1]Patent: WO2013/30802,2013,A1 .

18
[ 2840-29-1 ]
[ 41302-34-5 ]
C₁₄H₁₂BrNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polyphosphoric acid; In 1,4-dioxane; at 130℃; for 5h;Inert atmosphere;	A mixture of methyl 2-oxocyclohexanecarboxylate (1.70 g, 10 mmol), <strong>[2840-29-1]3-amino-4-bromobenzoic acid</strong> (2.16 g, 10 mmol), polyphosphoric acid (15 g) and dioxane (12 mL) was heated at 130 C for 5 hours. After cooling to room temperature, NaOAc-3H2O (27 g) was added and the pH~3. Then the mixture was diluted with water and the resulting precipitate was collected by filtration and dried. The solid was suspended in methanol (80 mL) and SOCl2 (16 mL) was added at 0-15 C, the mixture was stirred at reflux for 5 hours. After cooling to room temperature, the mixture was concentrated and treated with water (100 mL), extracted with ethyl acetate (3x100 mL), the organic layer was separated, and concentrated to afford the crude product. Then the mixture was purified by chromatography column on silica gel (eluted withCH2Cl2 /MeOH) to afford methyl 4-bromo-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylatet (2.20 g). MS (ESI) m/e [M+1]+336. A mixture of methyl 4-bromo-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylate (0.19 g, 0.56 mmol), MeOH (20 mL), and Pd/C (5% Pd on carbon, 50% water, 0.05 g) were stirred at room temperature under an atmosphere of hydrogen for 6 hours. The mixture was filtered through celite and the filtrate was concentrated to give crude methyl 9-oxo-5,6,7,8,9,10- hexahydroacridine-1-carboxylate (0.22 g), which was used to next step without further purification. To the solution of the crude methyl 9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylate in DMA (4 mL) was added hydrazine hydrate (4 mL) at room temperature, and the mixture was heated at 130 C for4.0 h. The reaction mixture was cooled to room temperature and stirred for another 12 hours. Then the mixture was filtered and recrystallized from MeOH (twice) to give the product (20 m g, 15%) as a yellow solid.
	With polyphosphoric acid; In 1,4-dioxane; at 130℃; for 5h;	A mixture of methyl 2-oxocyclohexanecarboxylate (1.70 g, 10 mmol), <strong>[2840-29-1]3-amino-4-bromobenzoic acid</strong> (2.16 g, 10 mmol), polyphosphoric acid (15 g) and dioxane (12 mL) was heated at 130 C. for 5 hours. After cooling to room temperature, NaOAc.3H2O (27 g) was added and the pH?3. Then the mixture was diluted with water and the resulting precipitate was collected by filtration and dried. The solid was suspended in methanol (80 mL) and SOCl2 (16 mL) was added at 0-15 C., the mixture was stirred at reflux for 5 hours. After cooling to room temperature, the mixture was concentrated and treated with water (100 mL), extracted with ethyl acetate (3*100 mL), the organic layer was separated, and concentrated to afford the crude product. Then the mixture was purified by chromatography column on silica gel (eluted with CH2 Cl2/MeOH) to afford methyl 4-bromo-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylatet (2.20 g).

References: [1]Patent: WO2013/97226,2013,A1 .Location in patent: Page/Page column 39; 40.
[2]Patent: US2015/18356,2015,A1 .Location in patent: Paragraph 0237.

19
[ 2840-29-1 ]
[ 1446262-29-8 ]

References: [1]Patent: WO2013/97226,2013,A1 .
[2]Patent: US2015/18356,2015,A1 .
[3]Patent: TWI588144,2017,B .

20
[ 2840-29-1 ]
[ 1446262-49-2 ]

References: [1]Patent: WO2013/97226,2013,A1 .
[2]Patent: US2015/18356,2015,A1 .

21
[ 2840-29-1 ]
[ 1446262-50-5 ]

References: [1]Patent: WO2013/97226,2013,A1 .
[2]Patent: US2015/18356,2015,A1 .
[3]Patent: TWI588144,2017,B .

22
[ 2840-29-1 ]
[ 1585969-87-4 ]

References: [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 343 - 351.

23
[ 2840-29-1 ]
[ 1585969-79-4 ]

References: [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 343 - 351.

24
[ 67-56-1 ]
[ 2840-29-1 ]
[ 46064-79-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With thionyl chloride; at 0℃; for 24h;Reflux;	General procedure: A solution of the appropriate 2-aminobenzoic acid (1equiv) in MeOH was cooled to 0C followed by a dropwise addition of thionyl chloride (2.5equiv). The mixture was refluxed for 24h. After evaporation of the solvent and neutralization by addition of a saturated aqueous NaHCO3 solution, the mixture was extracted with EtOAc and the combined organic layers were dried over MgSO4. Purification by CC (n-hexane/EtOAc) provided the title compounds.

References: [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 343 - 351.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 2423 - 2435.

25
[ 2840-29-1 ]
[ 92-67-1 ]
3-amino-N-(biphenyl-4-yl)-4-bromobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	A mixture of <strong>[2840-29-1]3-amino-4-bromobenzoic acid</strong> (4.5 g, 20.8 mmol) and biphenyl-4-amine (7.1 g, 41.7 mmol, 2.0 equiv) in DMF (150 mL) was treated with propanephosphonic anhydride (50%, 24 mL, 41.7 mmol, 2.0 equiv), followed by diisopropylethylamine (18 mL, 104 mmol, 5.0 equiv). The resulting mixture was allowed to stir at room temperature for 24 h. The resulting mixture was treated with water (150 mL). The resulting solids were separated, washed with water, and dried at 50 C under reduced pressure to give impure 3-amino-N-(biphenyl-4-yl)-4-bromobenzamide (6.0 g, 79%). This material was used in subsequent reactions without further purification.1H-NM (300 MHz, DMSO-d6): delta [ppm] = 5.54 (s, 2H), 7.03 (dd, J=2.3, 8.1 Hz, 1H), 7.28-7.33 (m, 2H), 7.42 (t, J=7.7 Hz, 2H), 7.46 (d, J=8.1 Hz, 1 H), 7.60-7.65 (m, 4H), 7.83 (d, J=8.6 Hz, 2H), 10.21 (s, 1H).LC-MS (Method 3): Rt= 1.32 min; MS (ESIpos): m/z = 367 ([M+H]+, 100%); MS (ESIneg): m/z = 365 [M- H]-, 90%).

References: [1]Patent: WO2014/147182,2014,A2 .Location in patent: Page/Page column 85; 86.

26
[ 2840-29-1 ]
N-(biphenyl-4-yl)-4-bromo-3-[(morpholin-4-ylacetyl)amino]benzamide [ No CAS ]