112970-44-2|2-Bromo-3-methoxyaniline| Ambeed

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Quality Control of [ 112970-44-2 ] Purity: 98% SDS Specification

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Product Details of [ 112970-44-2 ]

CAS No. :	112970-44-2
Formula :	C₇H₈BrNO
M.W :	202.05
SMILES Code :	NC1=CC=CC(OC)=C1Br
MDL No. :	MFCD07787450
InChI Key :	TUNIZJPEKHLBPR-UHFFFAOYSA-N
Pubchem ID :	10910575

Safety of [ 112970-44-2 ]

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

Computational Chemistry of [ 112970-44-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	45.04
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.86
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	1.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.05
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	1.78
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.67
Solubility	0.434 mg/ml ; 0.00215 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.	-2.26
Solubility	1.1 mg/ml ; 0.00546 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	-3.02
Solubility	0.192 mg/ml ; 0.000948 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.18 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)	1.34

Application In Synthesis of [ 112970-44-2 ]

* 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 [ 112970-44-2 ]

[ 112970-44-2 ] Synthesis Path-Downstream 1~35

1
[ 54362-87-7 ]
[ 112970-44-2 ]
[1-(2-Bromo-3-methoxy-phenyl)-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 8365 - 8368.

2
[ 67853-37-6 ]
[ 112970-44-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; iron; In ethanol; for 1.5h;Reflux;	Step 1. Synthesis of 2-bromo-3-methoxyaniline (C23) Iron (1.94 g, 34 mmol) was added to a solution of 2-bromo-1-methoxy-3-nitrobenzene (2.50 g, 10.77 mmol) in ethanol (18 mL) and concentrated hydrochloric acid (1 mL), and the reaction was heated at reflux for 1.5 hours. The mixture was cooled to room temperature, filtered through Celite and concentrated in vacuo to afford the title compound as a solid. Yield: 2.57 g, 10.77 mmol, 100%. LCMS m/z 202.1 (M+1). 1H NMR (400 MHz, CD3OD) delta 3.77 (s, 3H), 6.30 (d, J=8.0 Hz, 1H), 6.43 (d, J=8.0 Hz, 1H), 6.98 (dd, J=8.0, 8.0 Hz, 1H).
96%	With iron; ammonium chloride; In ethanol; water; for 1h;Heating / reflux;	Iron powder (1.08 mol) and ammonium chloride (862 mmol) were added to a solution of the bromide (216 mmol) in ethanol (200 mL) and water (140 mL) and the reaction mixture was heated at reflux for 1 h. The suspension was filtered and concentrated and the residue was extracted with ethyl acetate (3*200 mL). The combined organic layers were dried (sodium sulfate) and concentrated to give the bromoaniline in 96% yield as a yellow liquid.
96%	With hydrogenchloride; iron; In ethanol; water; at 85℃; for 2h;	To a suspension of 2-bromo-1-methoxy-3-nitrobenzene (3.90 g, 16.81 mmol) and iron powder (2.82 g, 50.4 mmol) in EtOH (50 mL) was added concentrated HC1 (3.08 mL, 37.0 mmol). The mixture was heated at 85 C for 2.0 h. HPLC indicated a completion of the reaction. After cooled to room temperature, the solvent was removed under vacuum. The residue was suspended in EtOAc and saturated sodium bicarbonate.The insoluble material was removed by filtration through a pad of wet celite. The organic layer of the filtrate was collected, washed with brine, dried over sodium sulfate. After evaporation of solvent, Intermediate iSA (3.25 g, 16.09 mmol, 96 %yield) was obtained as brown oil. It was used for the next step without further purification. ?H NMR (500MHz, chloroform-d) 7.08 (t, J=8.1 Hz, 1H), 6.45 (dd, J8.0, 1.4 Hz, 1H), 6.34 (dd,J=8.3, 1.1 Hz, 1H), 3.89 (s, 2H); LC-MS: method A, RT = 1.21 mm, MS (ESI) m/z: 202.0 and 204.0 (M+H)

95%	With iron; ammonium chloride; In tetrahydrofuran; methanol; water; for 1h;Reflux;	2-bromo-1-methoxy-3-nitrobenzene (1 g, 4.31 mmol), Fe (1.68 g, 30.17 mmol) and NH4Cl (1.61 g, 30.17 mmol)were dissolved in THF (4 mL)/MeOH (4 mL)/H2O (2 mL) solution and stirred for 1 hour under reflux. After terminationof the reaction, the reaction solution was cooled to room temperature, diluted with saturated NaHCO3 solution andextracted with EtOAc. The extract solution was concentrated under reduced pressure and purified by column chromatography(eluent, EtOAc/Hex = 1/5) to obtain the title compound (0.83 g, 95 % yield).1H NMR (500 MHz, CDCl3) delta 7.05(dd, 1H), 6.42(d, 1H), 6.31(d, 1H), 3.86(s, 3H)
91%	With acetic acid;iron; In ethanol; for 3.5h;Heating / reflux;	2-Bromo-3-nitroanisole B3 (1.00 g; 4.31 MMOL) was dissolved in glacial acetic acid (11.0 mL) and ethanol (11.0 mL). To this solution was added iron powder (0.98 g; 17.5 MMOL). The mixture was stirred at reflux for 3.5 h and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2CI2 (3X 50 mL). The extracts were dried (NA2SO4), filtered and CONCENTRATED IN VACUO to afford the crude product, 2-bromo-3 methoxyaniline B4 (91 %; 0. 79 g) as a pale yellow oil. MS 201.8 (MH) + ; Homogeneity by HPLC (TFA) 220 nm: 95%.
91%	With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;	Step C:; 2-Bromo-3-nitroanisole 1b3 (1.00 g; 4.31 mmol) was dissolved in glacialacetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder(0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. Thereaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and theproduct extracted with CH2CI2 (3X 50 mL). The extracts were dried (Na2SO4), filteredand concentrated in vacua to afford the crude product, 2-bromo-3 methoxyaniline 1b4(91%; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA) (at)220nm: 95%
91%	With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;	2-Bromo-3-nitroanisole 1b3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder (0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2(3*50 mL). The extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-bromo-3 methoxyaniline 1b4 (91%; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA)a220 nm: 95%
91%	With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;	2-Bromo-3-nitroanisole 2b3 (1.00 g; 4.31 mmol) was dissolved in glacialacetic acid (11.0 mL )/ethanol (11.0 mL) and to the solution was added iron powder(0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. Thereaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 andthe product extracted with CH2CI2( 3X 50 mL). The extracts were dried (Na2SO4),filtered and concentrated in vacuo to afford the crude product, 2-bromo-3methoxyaniline 2b4 (91%; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+;Homogeneity by HPLC (TFA) (at) 220nm: 95%
91%		Step C; 2-Bromo-3-nitroanisole 2B3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder (0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 h and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 and the product extracted with CH2CI2 (3X 50 mL). The extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-bromo-3 methoxyaniline 2B4 (91%; 0.79 g) as a pale yellow oil. MS 201.8 (MH)+; Homogeneity by HPLC (TFA) (at) 220nm: 95%
89%	With water; iron; ammonium chloride; In tetrahydrofuran; at 70℃; for 2.5h;	A solution of 2-bromo-l-methoxy-3 -nitrobenzene (500 mg, 2.16 mmol) in CH3OH (5 mL) and THF (5 mL) was added to a solution OfNH4Cl (572 mg, 10.7 mmol) in water (5 mL). Then, iron (325 mesh, 601 mg, 10.7 mmol) was added and the resulting mixture was heated to 70 C under nitrogen. After 2.5 h, the reaction mixture was cooled to room temperature, filtered over kieselguhr, diluted with AcOEt, and successively washed with a saturated solution OfNaHCO3 in water and brine. The organic layer was dried (Na2SO4) and evaporated. The residue was triturated in CH2Cl2, the filtered to give 390 mg (89 %) of the target product 37 as a beige solid.

References: [1]Patent: US2012/252758,2012,A1 .Location in patent: Page/Page column 27.
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 9287 - 9295.
[3]Patent: US2007/78147,2007,A1 .Location in patent: Page/Page column 67.
[4]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 318.
[5]Patent: EP3239143,2017,A2 .Location in patent: Paragraph 0441.
[6]Patent: WO2004/103996,2004,A1 .Location in patent: Page 40-41.
[7]Patent: WO2006/7700,2006,A1 .Location in patent: Page/Page column 62.
[8]Patent: US2006/19905,2006,A1 .Location in patent: Page/Page column 24-25.
[9]Patent: WO2006/85,2006,A1 .Location in patent: Page/Page column 75-76.
[10]Patent: WO2007/9227,2007,A1 .Location in patent: Page/Page column 35.
[11]Patent: WO2007/14919,2007,A1 .Location in patent: Page/Page column 91.
[12]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176.
[13]Synthetic Communications,2007,vol. 37,p. 2777 - 2786.
[14]Bulletin of the Chemical Society of Japan,1978,vol. 51,p. 2437 - 2438.
[15]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

3
[ 112970-44-2 ]
[ 98-59-9 ]
[ 112970-49-7 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176.

4
[ 112970-44-2 ]
[ 74128-84-0 ]

Yield	Reaction Conditions	Operation in experiment
68%		35% HCl (3 mL) and ice (3 g) were added to <strong>[112970-44-2]2-bromo-3-methoxyphenylamine</strong> (0.83 g, 4.11 mmol) obtainedin Step A, and cooled to 0-5C. NaNO2 (0.31 g, 4.52 mmol)/H2O (2 mL) solution was slowly added thereto, and themixture was stirred at 0-5C for 20 minutes. Pre-prepared KI (6.82 g, 41.1 mmol)/H2O (10 mL) solution was slowly addeddropwise to the reaction solution, and the reaction was carried out at room temperature for 12 hours. After terminationof the reaction, NaOH solution was added thereto, and the reaction solution was extracted with DCM. The organic layerwas washed with saturated NaHCO3 aqueous solution and water. The extracted organic layer was concentrated underreduced pressure and purified by column chromatography (eluent, EtOAc/Hex = 1/10) to obtain the title compound (0.88g, 68 %).1H NMR (500 MHz, CDCl3) delta 7.48(d, 1H), 7.00(dd, 1H), 6.85(d, 1H), 3.87(s, 3H)

References: [1]Patent: EP3239143,2017,A2 .Location in patent: Paragraph 0442.
[2]Journal of the American Chemical Society,2004,vol. 126,p. 1150 - 1160.
[3]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890.

5
[ 168335-61-3 ]
[ 112970-44-2 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 1150 - 1160.
[2]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890.

6
[ 24424-99-5 ]
[ 112970-44-2 ]
C₁₇H₂₄BrNO₅ [ No CAS ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 7836 - 7846.

7
[ 112970-44-2 ]
[ 140-89-6 ]
[ 908355-82-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	In N,N-dimethyl-formamide; at 135℃; for 6h;Inert atmosphere;	A solution of Intermediate iSA (3.25 g, 16.09 mmol) and potassium 0-ethyl carbonodithioate (6.45 g, 40.2 mmol) in DMF (20 mL) was heated at 135 C under argon for 6.0 h. HPLC and LCMS indicated a completion of the reaction. The mixture was cooled to room temperature, diluted with 20 mL water, followed by addition of 30 mL 1.0 N HC1. The precipitate formed was collected by filtration, washed with water, dried under vacuum and then chased with toluene (3X) to yield Intermediate 15B (3.1 g, 15.71 mmol, 98 % yield) as a brown solid. It was used for the next step without further purification. ?H NMR (500MHz, DMSO-d6) 13.77 (br. s., 1H), 7.38 (t, J=8.1 Hz, 1H), 6.94 (t, J=8.1 Hz, 2H), 3.91 (s, 3H); LC-MS: method A, RT = 1.63 mm, MS (ESI) m/z:198.0(M+H).

References: [1]Patent: WO2018/13774,2018,A1 .Location in patent: Page/Page column 318; 319.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

8
[ 603-85-0 ]
[ 112970-44-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.
[2]Journal of Organic Chemistry,1988,vol. 53,p. 1170 - 1176.

9
[ 16554-45-3 ]
[ 112970-44-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.
[2]Bulletin of the Chemical Society of Japan,1978,vol. 51,p. 2437 - 2438.

10
[ 112970-44-2 ]
9-butyl-8-(7-methoxybenzothiazol-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

11
[ 112970-44-2 ]
[ 809231-02-5 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 7836 - 7846.

12
[ 112970-44-2 ]
[ 809231-05-8 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 7836 - 7846.

13
[ 112970-44-2 ]
[ 18798-64-6 ]