681465-85-0|Methyl 4-amino-3-isopropoxybenzoate| Ambeed

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Quality Control of [ 681465-85-0 ] Purity: 97% SDS Specification

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Product Details of [ 681465-85-0 ]

CAS No. :	681465-85-0
Formula :	C₁₁H₁₅NO₃
M.W :	209.24
SMILES Code :	O=C(OC)C1=CC=C(N)C(OC(C)C)=C1
MDL No. :	MFCD12168764
Boiling Point :	No data available
InChI Key :	AQIZZMSROAYWPJ-UHFFFAOYSA-N
Pubchem ID :	43380211

Safety of [ 681465-85-0 ]

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

Computational Chemistry of [ 681465-85-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.36
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	58.23
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	61.55 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.36
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	1.86
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.85
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.	1.65
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	1.56
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.86

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.34
Solubility	0.954 mg/ml ; 0.00456 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.	-2.77
Solubility	0.352 mg/ml ; 0.00168 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	-2.69
Solubility	0.432 mg/ml ; 0.00207 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.	-6.26 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)	1.87

Application In Synthesis of [ 681465-85-0 ]

* 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 [ 681465-85-0 ]

[ 681465-85-0 ] Synthesis Path-Downstream 1~35

1
[ 75-30-9 ]
[ 63435-16-5 ]
[ 681465-85-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With caesium carbonate; In acetone; for 10h;Heating / reflux;	4-Amino-3-isopropoxy-benzoic acid methyl ester (3-4). To a solution of 2.045 g (12.23 mmol) methyl 4-amino-3-hydroxybenzoate (3-3) in 40 ml acetone, 1.83 ml 2-iodopropane (18.34 mmol, 1.5 eq.) and 7.97g (24.45 mmol, 2.0 eq.) Cs2CO3 were added. The resulting mixture was refluxed for 10 h and 10 ml of concentrated ammonium hydroxide was added. The solution was refluxed for 30 min and then cooled to room temperature. The mixture was diluted with water and extracted with Et2O. The organic layers were combined and washed with brine then dried with MgSO4. The crude mixture was purified by column chromatography on silica gel (hexane/EtOAc=4/1) to yield 3-4 as a colorless oil (2.300g, 90%). 1H-NMR (400 MHz, CDCl3): delta=1.31 (d, 6H, J=6.07 Hz, 2CH3), 3.82 (s, 3H, CH3), 4.32 (s, 2H, NH2), 4.57 (m, 1H, CH), 6.62 (d, 1H, J=8.17 Hz), 7.44 (d, 1H, J=1.71 Hz), 7.50 (dd, 1H, J1=8.21 Hz, J2=1.80 Hz). 13C-NMR (100 MHz, CDCl3): delta=21.87, 51.43, 70.47, 113.10, 113.68, 118.81, 123.70, 142.22, 143.81, 167.23. HRMS (ESI) m/z: calcd. for C11H16NO3 210.1101, found 210.2032 (M++H).
60%	With caesium carbonate; In acetone; at 120℃; for 1h;Microwave;	Methyl3-hydroxy-4-aminobenzoate (ABCR: 100 mg, 0.60 mmol) & caesium carbonate (396 mg, 1.22 mmol) were taken up in acetone (4 mL) and 2-iodopropane (90 mul, 0.90 mmol) added and reaction heated in microwave (CEM discover; 150 W) to 120 C. and held for 30 mins A further aliquot of 2-iodopropane (90 mul, 0.90 mmol) was added and reaction heated again to 120 C. in microwave, holding for a further 30 minsThe reaction was repeated twice on a 0.89 mmol scaleReaction mixtures were combined and evaporated to dryness and the residue partitioned between, ethyl acetate (40 ml) and water (50 ml). The organic phase was separated and the aqueous re-extracted with ethyl acetate (40 ml). Combined organic extracts were washed with brine, dried over magnesium sulphate and evaporated to give a brown oil which was purified by column chromatography, on silica (40 g cartridge; ISCO companion) eluting with a rising gradient of 5-50% ethyl acetate in iso-hexane. Product containing fractions were combined and evaporated to dryness to afford the product as a yellow oil (301 mg, 60%)1H NMR (400.132 MHz, DMSO-D6) delta 1.28 (d, 6H), 3.75 (s, 3H), 4.53 (m, 1H), 5.51 (s, 2H), 6.66 (d, 1H), 7.31 (m, 1H), 7.37 (m, 1H); MS m/z 209.4 [M+H]+.

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.
[2]Patent: US2007/123592,2007,A1 .Location in patent: Page/Page column 8; sheet 1.
[3]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 115.
[4]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1375 - 1379.

2
[ 681465-85-0 ]
[ 681465-87-2 ]

Yield	Reaction Conditions	Operation in experiment
86%		4-Iodo-3-isopropoxy-benzoic acid methyl ester (3-5). To a solution of 0.75 ml H2SO4 (96% in water) in 30 ml H2O at 0 C., a solution of 2.300 g (11.00 mmol) 3-4 in 20 ml MeOH was added. To the mixture 0.93 g NaNO2 (13.45 mmol, 1.2 eq.) in 20 ml water was added dropwise over a 20 min period and then the solution was stirred at 0 C. for 15 min. To the resulting mixture, 3.66 g KI (22.01 mmol, 2 eq.) and 63.54 mg Cu (bronze) (1.00 mmol, 0.1 eq.) were added. The solution was refluxed for 8 h and then cooled to room temperature. MeOH was removed at reduced pressure. The mixture was extracted with CH2Cl2. The organic layers were combined and washed with a saturated Na2S2O3 (aq.) solution and brine and then dried with MgSO4. The crude material was purified by column chromatography on silica gel (hexane/EtOAc=4/1) to yield 3-5 as a yellowish oil (3.037 g, 86%). 1H-NMR (400 MHz, CDCl3): delta=1.24 (d, 6H, J=6.14 Hz, 2CH3), 3.74 (s, 3H, CH3), 4.48 (m, 1H, CH), 7.12 (dd, 1H, J1=8.10 Hz, J2=1.74 Hz), 7.26 (s, 1H), 7.65 (d, 1H, J=8.11 Hz). 13C-NMR (100 MHz, CDCl3): delta=21.35, 51.60, 71.27, 94.37, 113.14, 122.31, 130.63, 138.82, 155.98, 165.35. HRMS (ESI) m/z: calcd. for C11H14IO3 321.1325, found 321.1330 (M++H).

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.
[2]Patent: US2007/123592,2007,A1 .Location in patent: Page/Page column 8; sheet 1.
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1375 - 1379.

3
[ 946825-98-5 ]
[ 681465-85-0 ]
methyl 4-[(6-cyclopentyl-2-methyl-3-oxo-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-9-yl)amino]-3-propan-2-yloxy-benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		To 10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 190 mg, 0.68 mmol) was added a solution of Methyl4-amino-3-propan-2-yloxy-benzoate (Intermediate 71, 145 mg, 0.69 mmol) in ethanol (4 mL), followed by water (12 mL). Concentrated hydrochloric acid (36%; 140 mul) was added and the reaction heated to 80 C., with stirring, overnight. The reaction was allowed to stand and cool overnight, before evaporating ethanol. The aqueous residue was diluted to 40 mL with water and the solution basified to pH 9 by addition of a few drops of aq. ammonia, The resultant emulsion was treated with a little brine and extracted with DCM (2×30 mL). The biphasic mixture was poured into a PTFE cup and the organic phase allowed to drip through under gravity. Evaporation of the organic phase afforded an amber gum, which was purified by flash chromatography on silica (40 g Si cartridge; ISCO companion), eluting with a rising gradient of 25-100% ethyl acetate in iso-hexane. Product containing fractions were combined and evaporated to give a colourless gum which was triturated with a small amount of diethyl ether and the resultant solid collected by suction filtration and dried to afford the title compound as a white solid (132 mg, 43%)1H NMR (400.132 MHz, DMSO-D6) delta 1.36 (d, 6H), 1.58-1.77 (m, 6H), 1.95 (m, 2H), 2.60 (m, 2H), 3.18 (s, 3H), 3.64 (m, 2H), 3.83 (s, 3H), 4.77 (m, 2H), 7.53 (m, 1H), 7.57 (m, 1H), 7.78 (s, 1H), 8.10 (s, 1H), 8.51 (d, 1H); MS m/z 452 [M+H]+.

References: [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 115.

4
[ 681465-85-0 ]
4-(1,2-dihydroxy-ethyl)-3-isopropoxy-N,N-diisopropyl-benzamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

5
[ 681465-85-0 ]
(S)-2-[(4-Formyl-3-isopropoxy-benzoyl)-isobutyl-amino]-3-methyl-butyric acid methyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

6
[ 681465-85-0 ]
(S)-2-[Isobutyl-(3-isopropoxy-4-vinyl-benzoyl)-amino]-3-methyl-butyric acid methyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

7
[ 681465-85-0 ]
(S)-2-[4-(1,2-Dihydroxy-ethyl)-3-isopropoxy-benzoyl]-isobutyl-amino}-propionic acid methyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

8
[ 681465-85-0 ]
N-isobutyl-2-isopropoxy-N-(1-methoxycarbonyl-2-methyl-propyl)-terephthalamic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

9
[ 681465-85-0 ]
(S)-2-[4-(1,2-Dihydroxy-ethyl)-3-isopropoxy-benzoyl]-isobutyl-amino}-3-methyl-butyric acid methyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

10
[ 681465-85-0 ]
(S)-2-{4-[Isobutyl-((S)-1-methoxycarbonyl-2-methyl-propyl)-carbamoyl]-2-isopropoxy-benzoylamino}-4-methyl-pentanoic acid methyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5463 - 5468.

11
[ 681465-85-0 ]
3-isopropoxy-4-vinylbenzoic acid chloride [ No CAS ]