18595-15-8|Methyl 3-amino-5-methylbenzoate| Ambeed

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Quality Control of [ 18595-15-8 ] Purity: 97% SDS Specification

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Product Details of [ 18595-15-8 ]

CAS No. :	18595-15-8
Formula :	C₉H₁₁NO₂
M.W :	165.19
SMILES Code :	O=C(OC)C1=CC(C)=CC(N)=C1
MDL No. :	MFCD09263222
InChI Key :	BPJRIMLTKIFIHS-UHFFFAOYSA-N
Pubchem ID :	21129903

Safety of [ 18595-15-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 18595-15-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	47.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.89
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	1.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.37
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.	1.64
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	1.44
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.56

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.02
Solubility	1.57 mg/ml ; 0.00951 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.	-2.16
Solubility	1.13 mg/ml ; 0.00684 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	-2.49
Solubility	0.531 mg/ml ; 0.00321 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.	-6.27 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	1.0
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)	1.42

Application In Synthesis of [ 18595-15-8 ]

* 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 [ 18595-15-8 ]

[ 18595-15-8 ] Synthesis Path-Downstream 1~26

Yield	Reaction Conditions	Operation in experiment
100%	With 5%-palladium/activated carbon; hydrogen; In methanol; at 20.0℃;	General procedure: To a solution of 3-nitromethyl benzoate (26.0 g, 144 mmol) in methanol (300 mL) was added Pd/C (2 g, 18.79mmol), the mixture was stirred under H2 at rt overnight. The reaction mixture was filtered through a Celite pad , the filtrate was concentrated in vacuo to get the title compound as a yellow oil (21.7 g, 100%).
99%	With palladium on activated charcoal; hydrogen; In ethanol; at 20.0℃;	General procedure: Pd/C (0.1 eq.) was added to a solution of the nitrobenzene (1.0 eq.) in EtOH (0.2 m). The suspension was degassed with H2and the reaction was stirred at room temperature upon complete consumption of the starting material. Then, the mixture was passed through a Celite pad and the filtrate was concentrated in vacuum. The product was used without any further purification.

3
[ 58530-13-5 ]
[ 18595-15-8 ]

Yield	Reaction Conditions	Operation in experiment
		[0204] The title compound was obtained by the method used in the preparation of 3- {2- [5-CYCLOHEXYL-L- (3, 3-DIMETHYL-2-OXO-BUTYL)-2-OXO-1, 2-DIHYDRO-3H-1, 3,4-benzotriazepin-3-yl]- ACETYLAMINO}-BENZOIC acid methyl ester (Example 1) except that 3-amino-5-methyl-benzoic acid methyl ester (prepared in three steps from 4-BROMO-3-METHYLBENZOIC acid) was used instead OF 3- amino-benzoic acid methyl ester in step e, followed by reaction of the product obtained, in place of 3- {2- [5-cyclohexyl-1- (3, 3-dimethyl-2-oxo-butyl)-2-oxo-1, 2-dihydro-3H-1, 3,4-benzotriazepin- 3-YL]-ACETYLAMINO}-BENZOIC acid methyl ester (Example 1), according to the method of Example 2. H NMR (CDC13) 8.44 (1H, s), 7. 87 (1H, s), 7.62 (2H, m), 7.53-7. 47 (2H, m), 7.34-7. 28 (1H, m), 7.05 (1H, d, 8. 1), 4. 81-4. 58 (2H, m), 4.26-4. 19 (2H, m), 2.84-2. 80 (1H, m), 2.39 (3H, s), 2.05-173 (6H, m), 1.41-1. 19 (13H, m). The compound was further characterised as the N- methyl-D-glucamine salt. Found C 58.77, H 7.70, N 9.33% ; C30H36N4OSUC7H17NOS1. 5H2O requires C 58. 87, H 7. 48, N 9.28%.

References: [1]Patent: WO2004/101533,2004,A1 .Location in patent: Page 71-72.

4
[ 476011-71-9 ]
[ 18595-15-8 ]
[ 1562519-58-7 ]

Yield	Reaction Conditions	Operation in experiment
25%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60.0℃; for 16.0h;	Intermediate H4: Methyl 3-((4-((4-aminonaphthalen-1 -yl)oxy)pyrimidin-2-yl)a methylbenzoate. Intermediate G2 To a solution of Intermediate G2 (806 mg, 2.97 mmol) and methyl 3-amino-5-methyl benzoate (490 mg, 2.97 mmol) in DMF (20 mL) was added p-TSA (1.13 g, 5.93 mmol) and the reaction mixture heated to 60C for 16 hr. After cooling to RT, the mixture was partitioned between EtOAc (30 mL) and saturated aq NaHC03 (30 mL). The organic phase was separated and was washed with water (30 mL) and brine (40 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12.0 g, 0-100% EtOAc in isohexane, gradient elution) to afford the title compound, Intermediate 4, as a red oil (680 mg, 25%); R< 2.13 min (Method 2 acidic); m/z 401 (M+H)+, (ES+).

References: [1]Patent: WO2014/27209,2014,A1 .Location in patent: Page/Page column 94.

5
[ 18595-15-8 ]
[ 1562518-97-1 ]

References: [1]Patent: WO2014/27209,2014,A1 .

6
[ 18595-15-8 ]
[ 1562519-22-5 ]

References: [1]Patent: WO2014/27209,2014,A1 .

7
6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylic acid [ No CAS ]
[ 18595-15-8 ]
methyl 3-(6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxamido)-5-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48 mg	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20.0℃; for 16.0h;	A solution of 6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-7-(l,3,5- trimethyl- lH-pyrazol-4-yl)- lH-indole-2-carboxylic acid (100 mg, 0.200 mmol), methyl 3- amino-5-methylbenzoate (36 mg, 0.220 mmol), DMAP (49 mg, 0.400 mmol) and EDC (77 mg, 0.400 mmol) in DCM (4 mL) was stirred at rt for 16 h. The reaction mixture was concentrated in vacuo, and the residue was purified by silica gel flash chromatography (ISCO, 0- 60% EtO Ac/Hex gradient) to give the title compound (48 mg, 0.074 mmol). MS(ES) 647.1 (M+H).

References: [1]Patent: WO2015/148854,2015,A1 .Location in patent: Paragraph 00691.

8
[ 18595-15-8 ]
methyl 3-(8-chloro-11-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1-oxo-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4,5-dihydro-1H-[1,4]diazepino[1,2-a]indol-2(3H)-yl)-5-methylbenzoate [ No CAS ]

References: [1]Patent: WO2015/148854,2015,A1 .

9
[ 18595-15-8 ]
3-(8-chloro-11-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1-oxo-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-4,5-dihydro-1H-[1,4]diazepino[1,2-a]indol-2(3H)-yl)-5-methylbenzoic acid [ No CAS ]

References: [1]Patent: WO2015/148854,2015,A1 .

10
[ 4331-54-8 ]
[ 18595-15-8 ]
C₁₇H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		14.22 g (100 mmol) of compound II-1 was refluxed in 50 mL of thionyl chloride for 5 hours and then excess thionyl chloride was removed and the resulting residue was dissolved in 20 mL of dry dichloromethane for later use.14.22 g (100 mmol) of compound III-I and 30.36 g (300 mmol) of triethylamine were dissolved in methylene chloride, and the mixture was stirred with cooling in an ice-water bath. Then, a solution ofII-1 acid chloride solution, after the addition was completed, stirring was continued overnight at room temperature.The reaction mixture was poured into 500 mL of ice water, stirred and extracted with 100 mL × 3 dichloromethane. The combined extracts were washed with brine, dried over anhydrous sodium sulfate,The hair was evaporated to dryness and the residue was purified by column chromatography to afford pure product IV-1.

References: [1]Patent: CN104447501,2017,B .Location in patent: Paragraph 0029; 0030; 0031.

11
[ 18595-15-8 ]
C₁₆H₂₁NO₃ [ No CAS ]

References: [1]Patent: CN104447501,2017,B .

12
[ 18595-15-8 ]
C₂₂H₂₇N₃O₂ [ No CAS ]

References: [1]Patent: CN104447501,2017,B .

13
[ 10147-36-1 ]
[ 18595-15-8 ]
C₁₅H₂₃NO₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;Reflux;	General procedure: A solution of aniline (1.0 eq.) and Et3N (2.2 eq.) in dry DCM (0.25 m) was cooled to 0C and the corresponding sulfonyl chloride was added dropwise. After complete addition the ice bath was removed and the solution was stirred at room temperature for ~1 h. The solution was then diluted with water, extracted with EtOAc and the combined organic layers were dried over Na2S04. The solvent was removed under reduced pressure and the product was purified via flash chromatography (Si02, nHex/EtOAc 9/1 ).

References: [1]Patent: WO2018/134254,2018,A1 .Location in patent: Page/Page column 32; 34.

14
[ 18595-15-8 ]
[ 4635-59-0 ]
C₁₂H₁₃NO₃ [ No CAS ]