102169-44-8|4-Bromo-5-methylbenzene-1,2-diamine| Ambeed

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Quality Control of [ 102169-44-8 ] Purity: 95% SDS Specification

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Product Details of [ 102169-44-8 ]

CAS No. :	102169-44-8
Formula :	C₇H₉BrN₂
M.W :	201.06
SMILES Code :	NC1=CC(C)=C(Br)C=C1N
MDL No. :	MFCD16987757
InChI Key :	BYYYESJDKPVYGB-UHFFFAOYSA-N
Pubchem ID :	22478120

Safety of [ 102169-44-8 ]

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

Computational Chemistry of [ 102169-44-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	2.0
Molar Refractivity	47.92
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.04 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.53
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	1.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.94
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.	1.91
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	1.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.7

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.55
Solubility	0.565 mg/ml ; 0.00281 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.	-2.33
Solubility	0.951 mg/ml ; 0.00473 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	-2.92
Solubility	0.24 mg/ml ; 0.00119 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	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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.38 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	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)	1.37

Application In Synthesis of [ 102169-44-8 ]

* 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 [ 102169-44-8 ]

[ 102169-44-8 ] Synthesis Path-Downstream 1~35

1
[ 64-18-6 ]
[ 102169-44-8 ]
[ 116106-16-2 ]

References: [1]Gazzetta Chimica Italiana,1958,vol. 88,p. 13,22.

2
[ 40371-63-9 ]
[ 102169-44-8 ]

References: [1]Journal of the Chemical Society,1953,p. 2816,2819.

3
2-bromo-4,5-dinitro-toluene [ No CAS ]
[ 102169-44-8 ]

References: [1]Journal of the Chemical Society,1953,p. 2816,2819.

4
[ 102169-44-8 ]
[ 431-03-8 ]
6-bromo-2,3,7-trimethyl-quinoxaline [ No CAS ]

References: [1]Journal of the Chemical Society,1953,p. 2822,2827.

5
[ 7745-93-9 ]
[ 102169-44-8 ]

References: [1]Journal of the Chemical Society,1953,p. 2816,2819.

6
[ 102169-44-8 ]
6-bromo-2,3,7-trimethyl-quinoxaline-1,4-dioxide [ No CAS ]

References: [1]Journal of the Chemical Society,1953,p. 2822,2827.

7
[ 102169-44-8 ]
[ 95-92-1 ]
[ 860503-17-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	at 40℃; for 0.5h;Microwave irradiation;	B. 6-Bromo-1,4-diethyl-7-methyl-1,4-dihydro-quinoxaline-2,3-dione (Compound 24B); Compound 24A (160 mg) in 1 mL of diethyl oxalate was heated in microwave at 140 C. for 30 min. Reaction was then cooled to rt, diluted with hexanes and resulting dark brown solid (164 mg, 81%) was collected by filtration. Solution of above intermediate (164 mg, 1 eq.) and ethyl iodide (0.52 mL, 10 eq.) in 3 mL of anhydrous DMSO was cooled on ice and crushed into powder KOH (144 mg, 4.0 eq.) was added slowly. Reaction was stirred on ice for 1 hour and at rt for another hour. Reaction was then partitioned between CH2Cl2 and water. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo. Crude was purified by column chromatography (40:60 hexane/EtOAc) to obtain 157 mg (78 %) of product. MS (electrospray): mass calculated for C13H15BrN2O2, 311.17; m/z found 312.2, [M+H]+.

References: [1]Patent: US2007/78129,2007,A1 .Location in patent: Page/Page column 29.

8
[ 89-62-3 ]
[ 102169-44-8 ]

Yield	Reaction Conditions	Operation in experiment
83%		Example 24; 3-[3-(1,4-Diethyl-7-methyl-2,3-dioxo-1,2,3,4-tetrahydro-quinoxalin-6-yl)-4-trifluoromethoxy-phenyl]-acrylic acid (Compound 24); A. 4-Bromo-5-methyl-benzene-1,2-diamine (Compound 24A); To the solution of 4-methyl-2-nitro-phenylamine (1 g, 1 eq.) in 15 mL of acetic acid was added NBS (1.4 , 1.2 eq.). The reaction was allowed to stir for 2.5 hours. Reaction was then diluted with 15 mL of water and Zn dust (1.29 g, 3 eq.) was added. Reaction was stirred for 1 hour, filtered and then pH was adjusted to 7 with ammonia. The aqueous layer was extracted with CH2Cl2 twice, dried over Na2SO4, concentrated and adsorbed on silica. Purification by flash column chromatography (60:40 hexanes/EtOAc) afforded 1.1 g (83 %) of product as off-white solid. MS (electrospray): mass calculated for C7H9BrN2, 201.06; m/z found 202.2, [M+H]+.

References: [1]Patent: US2007/78129,2007,A1 .Location in patent: Page/Page column 29.

9
trans-1,4-dioxane-2,3-diol [ No CAS ]
[ 102169-44-8 ]
6-bromo-7-methyl-quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol; at 20℃;	1.00 g (4.973 mmol) of the compound from example 39A was dissolved in 50 ml ethanol and 0.59 g (4.973 mmol) £ra«s-2,3-dihydroxy-l,4-dioxane was added. It was stirred overnight at room temperature. The reaction mixture was concentrated in a rotary evaporator at reduced pressure, taken up in ethyl acetate and purified on silica gel. We obtained 994 mg (84% of theor.) of the target compound.LC-MS (method 3): Rt = 1.65 min; MS (EIpos): m/z = 224 [M+H]+.1H-NMR (400 MHz, DMSO-D6): delta [ppm] = 2.60 (s, 3H), 8.11 (s, IH), 8.39 (s, IH), 8.92 (d, IH), 8.96 (d, IH).

References: [1]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 82.

10
[ 827-32-7 ]
[ 102169-44-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tin(ll) chloride; In ethanol; at 70℃;	4.OO g (17.312 mmol) of the compound from example 38A was dissolved in 100 ml ethanol and 15.63 g (69.248 mmol) of tin(II) chloride dihydrate was added. The mixture was stirred overnight at 70C. After cooling, water was added, it was made weakly alkaline with saturated aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The residue was dried under high vacuum. We obtained 3.23 g (89% of theor.) of the target compound.LC-MS (method 1): R, = 1.07 min; MS (EIpos): m/z = 201 [M+H]+.IH-NMR (400 MHz, DMSO-D6): delta [ppm] = 2.08 (s, 3H), 4.51 (s, 2H), 4.52 (s, 2H), 6.43 (s, IH), 6.66 (s, IH).

References: [1]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 81-82.

11
[ 506-68-3 ]
[ 102169-44-8 ]
[ 1388031-31-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	In water; acetonitrile; at 0 - 20℃;	Step A6-bromo-5-m zol-2-[00228] A cooled 0 C solution of 4-bromo-5-methylbenzene-1 ,2-diamine (0.86 g, 4.28 mmol) in acetonitrile (4 mL) and water (2 mL) was treated with cyanogen bromine (0.498 g, 4.70 mmol). The reaction mixture was allowed to warm slowly to room temperature and stir overnight. The reaction mixture was partitioned between DCM (100 mL) a sat. NaHCC^ solution (100 mL) and water (20 mL). The organic layer was dried with Na2SC>4, filtered and concentrated to obtain a brown solid. 67-1 The aqueous layer was filtered to yield a light tan solid. The is^SC^ contained a tan solid as well. The salts were dissolved in water, sonicated then filtered to yield a pink solid. Spectra of the pink solid and the material from the aqueous filtration were comparable so the samples were combined to yield 6-bromo-5-methyl-1 H- benzo[d]imidazol-2-amine as a light tan solid (825 mg, 3.28 mmol, 77 % yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 10.83 (br. s., 1 H) 7.21 - 7.40 (m, 1 H) 7.02 - 7.16 (m, 1 H) 6.67 (br. s., 2 H) 2.24 - 2.39 (m, 3 H). LCMS: m/z 225.9 (M+H+).

References: [1]Patent: WO2012/174312,2012,A2 .Location in patent: Page/Page column 159.

12
[ 102169-44-8 ]
[ 1416336-53-2 ]
[ 1416336-54-3 ]

References: [1]Patent: WO2012/174312,2012,A2 .

13
[ 102169-44-8 ]
5-(2-amino-1-benzyl-5-methyl-1H-benzo[d]imidazol-6-yl)-N-(tert-butyl)-2-methoxypyridine-3-sulfonamide trifluoro acetate [ No CAS ]

References: [1]Patent: WO2012/174312,2012,A2 .

14
[ 496-72-0 ]
[ 102169-44-8 ]

References: [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866.

15
[ 70376-38-4 ]
[ 102169-44-8 ]

References: [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866.

16
[ 335342-96-6 ]
[ 102169-44-8 ]

References: [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866.

17
[ 102169-44-8 ]
[ 2255-68-7 ]

References: [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866.

18
[ 102169-44-8 ]
5-(4-diphenylaminophenyl)-6-methylbenzo[c][1,2,5]thiadiazole [ No CAS ]

References: [1]Journal of Physical Chemistry A,2016,vol. 120,p. 1853 - 1866.

19
[ 102169-44-8 ]
Ν-α-[(trans-4-[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-(2-isopropyl-6-methyl-1H-benzimidazol-5-yl)-N-(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-D-phenylalaninamide [ No CAS ]