40800-65-5|Ethyl 4-amino-3-methylbenzoate| Ambeed

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Quality Control of [ 40800-65-5 ] Purity: 98% SDS Specification

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Product Details of [ 40800-65-5 ]

CAS No. :	40800-65-5
Formula :	C₁₀H₁₃NO₂
M.W :	179.22
SMILES Code :	CCOC(=O)C1=CC(C)=C(N)C=C1
MDL No. :	MFCD03788450
InChI Key :	JUKRQDBAJXYXIR-UHFFFAOYSA-N
Pubchem ID :	282796

Safety of [ 40800-65-5 ]

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

Computational Chemistry of [ 40800-65-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	51.9
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.	2.16
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	2.06
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.76
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.	1.94
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	1.8
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.	-2.39
Solubility	0.726 mg/ml ; 0.00405 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.	-2.79
Solubility	0.292 mg/ml ; 0.00163 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	-2.9
Solubility	0.223 mg/ml ; 0.00124 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.	-5.93 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)	1.52

Application In Synthesis of [ 40800-65-5 ]

* 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 [ 40800-65-5 ]

[ 40800-65-5 ] Synthesis Path-Downstream 1~35

1
[ 30650-90-9 ]
[ 40800-65-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃;	The compound (2) (10.45 g, 50 mmol) add to 60 ml EtOH of 150 ml single-port in the bottle, by adding 1.0 g 10% Pd/C anhydrous, hydrogen atmosphere react at the room temperature overnight, TLC monitoring basic completion of the reaction, the reaction solution is filtered, wash with methanol three times, the rotary evaporating the concentrated filtrate, to obtain compound (3) 8.2 g, yield: 92.0%
50%	With acetic acid; zinc; at 20℃; for 4h;	Step 1. Synthesis of 4-amino-3-methyl-benzoic acid ethyl ester To a solution of ethyl 3-methyl-4-nitrobenzoate (1.26 g, 6.00 mmol) in 12.0 mL of acetic acid was added zinc dust(s) (1.90 g, 30.0 mmol) in one portion at r.t. The reaction mixture was stirred at r.t. for 4 h then passed through a pad of celite. The filtrate was partitioned between ethyl acetate (100 mL) and saturated NaHCO3(aq) (50 mL). The organic layer was washed with brine (20 mL), dried over MgSO4 and concentrated to give a crude product which was purified by flash chromatography (ethyl acetate:hexane=1:3) to give the desired product as a white solid (540 mg, 50%). 1H NMR (CDCl3, 400 MHz) delta 7.77-7.74 (m, 2H), 6.69 (d, 1H), 4.49 (br s, 2H), 4.32 (q, 2H), 2.21 (s, 3H), 1.36 (t, 3H).

References: [1]European Journal of Organic Chemistry,2010,p. 4662 - 4670.
[2]Patent: CN108329269,2018,A .Location in patent: Paragraph 0087; 0088; 0093-0095.
[3]Patent: US2017/253569,2017,A1 .Location in patent: Paragraph 0367-0368.
[4]Chemische Berichte,1895,vol. 28,p. 597.
[5]Journal of the American Chemical Society,2018,vol. 140,p. 12457 - 12468.

2
[ 40800-65-5 ]
3-methyl-4-sulfinylamino-benzoic acid ethyl ester [ No CAS ]

References: [1]Chemische Berichte,1895,vol. 28,p. 597.

3
[ 40800-65-5 ]
[ 112-82-3 ]
[ 86410-39-1 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1393 - 1411.

4
[ 2486-70-6 ]
[ 40800-65-5 ]

References: [1]Helvetica Chimica Acta,1979,vol. 62,p. 271 - 303.

5
[ 40800-65-5 ]
[ 108-24-7 ]
[ 70204-39-6 ]

References: [1]Helvetica Chimica Acta,1979,vol. 62,p. 271 - 303.

Yield	Reaction Conditions	Operation in experiment
87%		B. Ethyl 3-methyl-4-aminobenzoate A mixture of the product prepared accordIng to Example 1050e Part A (183.96 g, 880 mol), tin (II) chloride hydrate (1025 g, 4.54 mol) and ethanol (3500 mL) was heated at reflux for 2 h. The mixture was cooled and diluted with water (3500 mL) and the pH was adjusted to 8.5. The mixture was diluted further with additional water, and extracted with ethyl acetate. The organic extracts were dried (MgSO4), filtered and concentrated to provide the title product (136.62 g, 87%) as an off-white solid: mp 76-78 C.; 1 H NMR (CDCl3) delta 7.78 (s, 1H), 7.76 (d, 1H), 6.63 (d, 1H), 4,31 (q, 2H), 3.99 (bs, 2H), 2.19 (s, 3H), 1.38 (t, 3H); High resolution mass spectrum (NH3 --CI) calculated (M+H+) 180.1025, found 180.1023.
87%		B. Ethyl 3-methyl-4-aminobenzoate. A mixture of the product prepared according to Example E-19 Part A (183.96 g, 880 mmol), tin (II) chloride hydrate (1025 g, 4.54 mol) and ethanol (3500 mL) was heated at reflux for 2 h. The mixture was cooled and diluted with water (3500 mL) and the pH was adjusted to 8.5. The mixture was diluted further with additional water, and extracted with ethyl acetate. The organic extracts were dried (MgSO4), filtered and concentrated to provide the title product (136.62 g, 87%) as an off-white solid, mp 76-78 C.: 1H NMR (CDCl3) d 7.78 (s, 1H), 7.76 (d, 1H), 6.63 (d, 1H), 4.31 (q, 2H), 3.99 (bs, 2H), 2.19 (s, 3H), 1.38 (t, 3H); High resolution mass spectrum (NH3-CI) calculated (M+H+) 180.1025, found 180.1023.

7
[ 7719-09-7 ]
[ 40800-65-5 ]
[ 71-43-2 ]
3-methyl-4-sulfinylamino-benzoic acid ethyl ester [ No CAS ]

References: [1]Chemische Berichte,1895,vol. 28,p. 597.

8
[ 40800-65-5 ]
[ 108-24-7 ]
[ 808745-05-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	In toluene; at 20 - 90℃; for 2h;	(VI.2) 4-Amino-3-diethylaminomethyl-5-chloro-benzoic acid x HCl; a) Ethyl-4-acetylamino-3-methyl-benzoate; To a suspension of ethyl-4-amino-3-methyl-benzoate (537 g; 3.0 mol; preparation described in Helv. Chim. Acta 62 (1979) 271-303) in 3 litres of toluene is added dropwise acetic anhydride (320 g; 3.14 mol) while stirring at ambient temperature. The reaction mixture is then heated for 2 hours at 85-90C. The crystals formed upon cooling to ambient temperature are filtered off with suction, dried and recrystallized from ethanol. Yield: 590 g (89%) Melting point 133-135C.
	With dmap; In DMF (N,N-dimethyl-formamide); at 20℃; for 4h;	To a solution of <strong>[40800-65-5]ethyl 4-amino-3-methylbenzoate</strong> (7.43 g)in DMF ..(35 ml) were added DMAP (506 mg) and acetic anhydride(4.66 g) at ambient temperature. After stirring for 4 hours,the reaction mixture was diluted with water (40 ml) andextracted with EtOAc (4 x 60 ml). The combined organicextracts were washed with saturated NaHCOs (2 x 30 ml) andbrine (3 x 100 ml) . The organic layer was dried over MgSC>4 andfiltered. Evaporation gave a residue which was triturated withEtOAc - n-hexane to give ethyl 4-(acetylamino)-3-methylbenzoate(4.324 g) as white crystals. The filtrate was evaporated andtriturated with EtOAc - n-hexane to give second crop (1.64 g).NMR(DMSO-d6,8) :. 1.31 (3H, t, J = 7.1Hz), 2.11 (3H, s) , 2.28(3H, s), 4.29 (2H, q, J = 7.1 Hz), 7.7-7.8 (3H, m), 9.37 (1H,br s) .MS: 244 (M+Na). .

References: [1]Patent: EP1645556,2006,A1 .Location in patent: Page/Page column 10.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 41 - 58.
[3]Patent: WO2004/108686,2004,A2 .Location in patent: Page 107.

9
[ 40800-65-5 ]
[ 244768-32-9 ]
[ 943826-94-6 ]