174579-31-8|tert-Butyl 2-(4-aminophenyl)acetate| Ambeed

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Quality Control of [ 174579-31-8 ] Purity: 98% SDS Specification

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Product Details of [ 174579-31-8 ]

CAS No. :	174579-31-8
Formula :	C₁₂H₁₇NO₂
M.W :	207.27
SMILES Code :	CC(C)(C)OC(=O)CC1=CC=C(N)C=C1
MDL No. :	MFCD06245494
InChI Key :	OOPUFXZJWLZPLC-UHFFFAOYSA-N
Pubchem ID :	2760930

Safety of [ 174579-31-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 174579-31-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	61.17
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.	2.41
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	2.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.16
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.	2.25
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	2.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.42
Solubility	0.782 mg/ml ; 0.00377 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.	-2.74
Solubility	0.381 mg/ml ; 0.00184 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	-3.35
Solubility	0.0928 mg/ml ; 0.000448 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.	-6.14 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.	1.0 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)	1.66

Application In Synthesis of [ 174579-31-8 ]

* 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 [ 174579-31-8 ]

[ 174579-31-8 ] Synthesis Path-Downstream 1~35

1
[ 75-21-8 ]
[ 174579-31-8 ]
[ 174579-27-2 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1100 - 1105.

2
[ 29704-38-9 ]
[ 174579-31-8 ]

Yield	Reaction Conditions	Operation in experiment
51%	With palladium 10% on activated carbon; hydrogen; In methanol; for 3h;	Compound 2- (4-nitrophenyl) t-butyl acetate 55b (5 g, 21 mmol) was dissolved in methanol (30 mL),Then 10% palladium on carbon (1 g) was added and stirred for 3 hours under a hydrogen atmosphere.After the reaction was completed, the filtrate was filtered, and the solvent was removed under reduced pressure.The target product tert-butyl 2- (4-aminophenyl) acetate 55c (2.25 g, yellow oil) was obtained in a yield of 51%.

References: [1]Patent: CN110818641,2020,A .Location in patent: Paragraph 0700-0702; 0707-0710.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 1100 - 1105.

3
[ 51656-70-3 ]
[ 106-40-1 ]
[ 174579-31-8 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 11176 - 11177.

4
[ 174579-31-8 ]
[ 119054-10-3 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1100 - 1105.

5
[ 174579-31-8 ]
[ 10477-72-2 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1100 - 1105.

7
[ 174579-31-8 ]
[ 328267-59-0 ]
[ 934464-17-2 ]

Yield	Reaction Conditions	Operation in experiment
		synthesis of a long wavelength BODDPY conjugated potassium sensor involves the formation of a Schiffs base using aldehyde 1 with t-butyl-4- aminophenylacetate 2 and in situ reduction to produce secondary amine 3. formation of a Schiff s base using aldehyde 1 with t-butyl-4-aminopehnylacetate 2 and in situ reduction to produce a secondary amine 3.

References: [1]Patent: WO2007/44866,2007,A2 .Location in patent: Page/Page column 62; 63.

8
[ 1670-82-2 ]
[ 174579-31-8 ]
[ 1034776-13-0 ]
1H-indole-6-carboxylic acid [1,2,3]triazolo[4,5-b]pyridin-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; HATU; In N,N-dimethyl-formamide; at 60℃; for 18h;	A solution of indole-6-carboxylic acid (2.00 g, 12.40 mmol) in dimethylformamide (20.00 mL) under argon was treated with N-methyl morpholine (6.82 mL, 62.04 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate (HATU) (7.08 g, 18.62 mmol) and <strong>[174579-31-8](4-amino-phenyl)-acetic acid tert-butyl ester</strong> (2.57 g, 12.40 mmol). The mixture was warmed at 60 C. and stirred for 18 hours. After cooling to room temperature, water (15.00 mL) was added. The resulting slurry was extracted with ethyl acetate and the combined organic phases washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), to yield pure {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester (0.51 g) and a mixture of {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester and 1H-indole-6-carboxylic acid [1,2,3]triazolo[4,5-b]pyridin-3-yl ester (3.41 g). This was dissolved in tetrahydrofuran (34.00 mL) and treated with 1N NaOH. The mixture was stirred at room temperature for 4 hours, then extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulphate and evaporated, and the residue triturated in ether to afford {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester (1.36 g), which was combined with the aliquot obtained by flash chromatography. Total yield of {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester, 1.87 g (43%), MS (mass spectrometry) (ISP): m/e=351.3 (M+H). As used herein (M+H)=the molecular weight of the compound plus a proton.

References: [1]Patent: US2008/153805,2008,A1 .Location in patent: Page/Page column 10.

9
[ 59368-16-0 ]
[ 174579-31-8 ]
[ 1246636-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; acetonitrile; at 70℃; for 15h;	Crude 6-(bromomethyl)-2,4-pteridinediamine (Step 1 , Example 19)(80 mg, 0.392 mmol), <strong>[174579-31-8]tert-butyl 2-(4-aminophenyl)acetate</strong> (228 mg, 1.12 mmol), and K2CO3 (542 mg, 3.9 mmol) are dissolved in a DMF (1 mL), CH3CN (3 mL) mixture and heated to 70 0C overnight (15 h). The crude reaction mixture is filtered and washed with MeOH ( 30 mL). The filtrate is concentrated by rotoevaporation, dissolved in minimum amount of MeOH (5 mL), and filtered again by syringe filter (0.45 um) for purification by prep HPLC using Method 1. The desired fractions are combined and concentrated to give 15 mg of tert-butyl 2-(4- ((2,4-diaminopteridin-6-yl)methylamino) phenyl)acetate (Yield; 10%).

References: [1]Patent: WO2010/110907,2010,A1 .Location in patent: Page/Page column 60.

10
[ 75-44-5 ]
[ 174579-31-8 ]
[ 181519-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In dichloromethane; water; toluene; at 5 - 20℃; for 0.5h;	Preparation of the Isocyanate4-Aminophenyl acetic acid tert-butyl ester (2.27 g, 10.95 mmol) was dissolved in dichloromethane (80 mL) and an aqueous solution of saturated sodium bicarbonate (80 mL) was added. The reaction mixture was cooled down to 5 C. using an ice bath and a solution of phosgene (2M in toluene, 11 mL, 22 mmol) was then added drop wise via a syringe. The reaction mixture was stirred at room temperature for 30 minutes and then worked up by extracting the aqueous phase twice with dichloromethane (50 mL). The organic layer was dried over sodium sulfate and evaporated to dryness in vacuo to yield 2.6 g (>100%, contains traces of toluene) of white solid which was clean enough by NMR for use in the next synthetic step.

References: [1]Patent: US2011/190267,2011,A1 .Location in patent: Page/Page column 52.

11
[ 174579-31-8 ]
[ 1314003-57-0 ]

References: [1]Patent: US2011/190267,2011,A1 .

12
[ 174579-31-8 ]
[ 1314003-16-1 ]

References: [1]Patent: US2011/190267,2011,A1 .

13
[ 79-04-9 ]
[ 174579-31-8 ]
[ 1388657-40-6 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 6391 - 6402.

14
[ 174579-31-8 ]
[ 90798-99-5 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 6391 - 6402.

15
tert-butoxycarbonylmethylzinc bromide tetrahydrofuran salt [ No CAS ]
[ 106-40-1 ]
[ 174579-31-8 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 8250 - 8266.

16
[ 6780-38-7 ]
[ 174579-31-8 ]
C₂₂H₂₂N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of N-phthaloylglycine 5 (1.0 equiv) in chloroform (0.2 M) was added thionyl chloride (1.5 equiv). The reaction mixture was refluxed for 4 hours, after which the solution was concentrated in vacuo. The mixture was then taken in THF (0.4 M) and cooled down to 0C in an ice bath. To this was added a solution of the suitably functionalized aniline 6a-e (1.2 equiv) and triethylamine (2.0M) in THF (0.4 M). The reaction mixture was then refluxed overnight, following which it was diluted with ethyl acetate and washed subsequently with 1N HCl and saturated NaHCO3. The ethyl acetate layer was concentrated in vacuo and the crude was used in the next step without purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5874 - 5877.

17
[ 174579-31-8 ]
[ 1469894-76-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5874 - 5877.

18
[ 174579-31-8 ]
[ 1469894-61-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5874 - 5877.

19
[ 174579-31-8 ]
[ 1469894-68-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5874 - 5877.

20
[ 174579-31-8 ]
[ 1469894-72-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5874 - 5877.

21
[ 5466-43-3 ]
[ 174579-31-8 ]
[ 1621294-35-6 ]