885519-05-1|Methyl 3-bromo-2-methyl-5-nitrobenzoate| Ambeed

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Quality Control of [ 885519-05-1 ] Purity: 97% SDS Specification

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Product Details of [ 885519-05-1 ]

CAS No. :	885519-05-1
Formula :	C₉H₈BrNO₄
M.W :	274.07
SMILES Code :	O=C(OC)C1=CC([N+]([O-])=O)=CC(Br)=C1C
MDL No. :	MFCD08273772
Boiling Point :	No data available
InChI Key :	KHYSOGYKNCNXIS-UHFFFAOYSA-N
Pubchem ID :	21907564

Safety of [ 885519-05-1 ]

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

Computational Chemistry of [ 885519-05-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	59.21
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	72.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.04
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	2.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.45
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.	1.88
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	0.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.31
Solubility	0.133 mg/ml ; 0.000486 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.	-3.83
Solubility	0.0409 mg/ml ; 0.000149 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	-3.09
Solubility	0.221 mg/ml ; 0.000807 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	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	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.	-6.08 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	2.0 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)	2.33

Application In Synthesis of [ 885519-05-1 ]

* 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 [ 885519-05-1 ]

[ 885519-05-1 ] Synthesis Path-Downstream 1~35

1
[ 99548-54-6 ]
[ 885519-05-1 ]
[ 894351-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid; at -30 - 10℃; for 0.5h;	EXAMPLE 128A Methyl 4'-amino-2-methyl-5-nitro-1,1'-biphenyl-3-carboxylate Example 1A (20 g, 87.3 mmol) was cooled to -5 C. and treated dropwise with H2SO4 (100 mL) at such a rate as to maintain the internal temperature below 10 C. The reaction mixture was cooled to -30 C. and treated dropwise with nitric acid (5.7 mL, 91.7 mmol) at such a rate as to maintain the internal temperature below -12 C. After the addition was complete the reaction flask was placed in an ice bath for 30 minutes and poured onto crushed ice. The resulting suspension was extracted twice with diethyl ether and the combined extracts were washed with aqueous NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to give 23 g of a mixture of methyl 3-bromo-2-methyl-5-nitrobenzoate and methyl 3-bromo-2-methyl-6-nitrobenzoate. Substitution of this mixture for Example 1C in Example 1D followed by purification by silica gel chromatography with 10 to 40% ethyl acetate/hexanes provided the desired product. 1H NMR (300 MHz, DMSO-d6) delta 2.46 (s, 3H), 3.91 (s, 3H), 5.36 (s, 2H), 6.67 (d, J=8.5 Hz, 2H), 7.07 (d, J=8.1 Hz, 2H), 8.06 (d, J=2.7 Hz, 1H), 8.41 (d, J=2.7 Hz, 1H).
	With sulfuric acid; nitric acid; In water; at -30 - 10℃; for 0.5h;	Example 1A (20g, 87.3 mmol) was cooled to -5 C and treated dropwise with H2SO4(100 mL) at such a rate as to maintain the internal temperature below 10 C. The reactionmixture was cooled to -30 C and treated dropwise with nitric acid (5.7 mL, 91.7 mmol) atsuch a rate as to maintain the internal temperature below -12 C. After the addition wascomplete the reaction flask was placed in an ice bath for 30 minutes and poured onto crushed ice. The resulting suspension was extracted twice with diethyl ether and the combinedextracts were washed with aqueous NaHCOs and brine, dried (MgSO4), filtered, andconcentrated to give 23g of a mixture of methyl 3-bromo-2-methyl-5-nitrobenzoate andmethyl 3-bromo-2-methyl-6-nitrobenzoate. Substitution of this mixture for Example 1C inExample ID followed by purification by silica gel chromatography with 10 to 40% ethylacetate/hexanes provided the desired product.

References: [1]Patent: US2005/26976,2005,A1 .Location in patent: Page/Page column 29.
[2]Patent: WO2004/108672,2004,A1 .Location in patent: Page 63; 64.

2
[ 1975-52-6 ]
[ 885519-05-1 ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

3
[ 67-56-1 ]
[ 1269292-02-5 ]
[ 885519-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; at 20 - 30℃; for 6.0h;Inert atmosphere;	The above reaction solution of 19b was added with 100 mL of methanol and continuously stirred for 6 hours.After the reaction was completed, the reaction solution was poured into 1L of water, and extracted with ethyl acetate(100 mL33). The organic phases were combined, washed successively with water (100 mL) and saturated sodiumchloride solution (200 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reducedpressure to obtain the crude title compound 19c (53 g) as a white solid, which was directly used in the next step withoutfurther purification.

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .Location in patent: Paragraph 0093; 0100-0101; 0199; 0200; 0201.

4
[ 885519-05-1 ]
methyl 3-bromo-5-hydroxy-2-methylbenzoate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

5
[ 885519-05-1 ]
3-bromo-5-mercapto-2-methylbenzoic acid [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

6
[ 885519-05-1 ]
methyl 3-bromo-5-(2, 2-diethoxyethoxy)-2-methylbenzoate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

7
[ 885519-05-1 ]
methyl 3-bromo-5-((2,2-diethoxyethyl)thio)-2-methylbenzoate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

8
[ 885519-05-1 ]
C₁₄H₁₉BrO₄S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

9
[ 885519-05-1 ]
methyl 6-bromo-5-methylbenzofuran-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

10
[ 885519-05-1 ]
methyl 6-bromo-5-methylbenzo[b]thiophene-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

11
[ 885519-05-1 ]
methyl 5-methyl-6-((tetrahydro-2H-pyran-4-yl) amino)benzofuran-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

12
[ 885519-05-1 ]
methyl 6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-methylbenzofuran-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

13
[ 885519-05-1 ]
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-methylbenzofuran-4-carboxamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

14
[ 885519-05-1 ]
methyl-5-methyl-6-((tetrahydro-2H-pyran-4-yl)amino)benzo[b]thiophene-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

15
[ 885519-05-1 ]
methyl 6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-methylbenzo[b]thiophene-4-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

16
[ 885519-05-1 ]
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-methylbenzo[b]thiophene-4-carboxamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

17
[ 885519-05-1 ]
6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-methylbenzofuran-4-carboxylic acid [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

18
[ 885519-05-1 ]
C₁₇H₂₁NO₃S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

19
[ 885519-05-1 ]
methyl 5-amino-3-bromo-2-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With iron; ammonium chloride; In ethanol; water; at 70℃; for 2.0h;Inert atmosphere;	Step 1 Methyl 5-amino-3-bromo-2-methylbenzoate Methyl 3-bromo-2-methyl-5-nitrobenzoate 4a (13 g, 47.3 mmol, prepared by a method disclosed in the patent application "") was added to 200 mL of ethanol and 50 mL of water. The mixture was heated to 70C, then ammonium chloride (20.6 g, 378 mmol) was added, and iron powder (13.3 g, 236 mmol) was added in batches. The reaction system was stirred for 2 hours at 70C. After the reaction was completed, the mixture was filtered through a pad of celite while hot. The filter cake was washed with hot ethanol, then the filtrate was combined and concentrated under reduced pressure. The residue was neutralized with saturated sodium bicarbonate solution, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with elution system B to obtain the title compound methyl 5-amino-3-bromo-2-methylbenzoate 4b (11.0 g, yield 95%) as a yellow solid.

References: [1]Patent: EP3378859,2018,A1 .Location in patent: Paragraph 0093; 0124-0125; 0202.
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

20
[ 885519-05-1 ]
6-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-methylbenzofuran-4-carboxamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.
[2]Patent: EP3378859,2018,A1 .

21
[ 885519-05-1 ]
C₂₆H₃₃N₃O₄ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

22
[ 885519-05-1 ]
C₂₅H₂₈F₃N₃O₄ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 98 - 102.

23
[ 885519-05-1 ]
methyl 3-bromo-2-methyl-5-(prop-2-yn-1-yloxy)benzoate [ No CAS ]