72220-50-9|2-(4-(Trifluoromethoxy)phenoxy)acetic acid| Ambeed

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Quality Control of [ 72220-50-9 ] Purity: 95% SDS Specification

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Product Details of [ 72220-50-9 ]

CAS No. :	72220-50-9
Formula :	C₉H₇F₃O₄
M.W :	236.14
SMILES Code :	OC(=O)COC1=CC=C(OC(F)(F)F)C=C1
MDL No. :	MFCD00052352
InChI Key :	QHSBEEUEIRDHCD-UHFFFAOYSA-N
Pubchem ID :	697705

Safety of [ 72220-50-9 ]

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

Computational Chemistry of [ 72220-50-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	5
Num. H-bond acceptors	7.0
Num. H-bond donors	1.0
Molar Refractivity	46.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.76 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.7
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	2.44
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.31
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.	1.24
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	1.73
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.08

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.79
Solubility	0.384 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 (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.25
Solubility	0.132 mg/ml ; 0.000557 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	-2.55
Solubility	0.666 mg/ml ; 0.00282 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.	-6.01 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.	0.56

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	0.0 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)	1.83

Application In Synthesis of [ 72220-50-9 ]

* 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 [ 72220-50-9 ]

[ 72220-50-9 ] Synthesis Path-Downstream 1~33

1
[ 39634-98-5 ]
[ 72220-50-9 ]
[ 219685-60-6 ]
<i>N</i>-{4-[(3-chloro-4-hydroxy-benzoyl)-hydrazonomethyl]-2-methoxy-phenyl}-2-(4-trifluoromethoxy-phenoxy)-acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5755 - 5775.

2
[ 72220-50-9 ]
1-(1-ethylpropyl)piperazine [ No CAS ]
1-[4-(1-ethyl-propyl)-piperazin-1-yl]-2-(4-trifluoromethoxy-phenoxy)-ethanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2833 - 2838.

3
[ 72220-50-9 ]
[ 710328-09-9 ]
<i>N</i>-[4-methyl-2-(4-methyl-piperazin-1-yl)-quinolin-6-yl]-2-(4-trifluoromethoxy-phenoxy)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4099 - 4102.

4
[ 72220-50-9 ]
[ 72220-51-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; for 14h;	Example 3; [0214] (4-Trifluoromethoxyphenoxy)-acetyl chloride: (4-Trifluoromethoxyphenoxy)- acetic acid (20.7 g, 88 mmol) was dissolved in thionyl chloride (100 mL). DMF (3 drops) was added to the solution. The solution was stirred for 14 hours. The thionyl chloride was removed in vacuo. The resulting oil was dissolved in dichloromethane, filtered through sodium sulfate and concentrate in vacuo to afford the title compound as a paste-like solid (21.8 g, 97% from the phenol) : MS (EI-GCMS) for C9H6C1F303: 254 (M+).
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 C. The solution was stirred for another 2 hrs at 25 C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.

References: [1]Patent: US6369049,2002,B1 .Location in patent: Example 8.
[2]Patent: WO2005/97765,2005,A1 .Location in patent: Page/Page column 273.
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6666 - 6672.

5
[ 771543-35-2 ]
[ 72220-50-9 ]
N-(cis-4-[(4-Methylquinolin-2-yl)amino]cyclohexyl}-2-[4-(trifluoromethoxy)phenoxy]-acetamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide;	Step A: Synthesis of N-[cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl)-2-[4-(trifluoromethoxy)phenoxy]-acetamide trifluoroacetate. To a solution of cis-N(4-methyl-quinolin-2-yl)-cyclohexane-1,4-diamine (25.5 mg, 0.1 mmol) in 0.5 mL DMF was added <strong>[72220-50-9]4-(trifluoromethoxy)phenoxyacetic acid</strong> (23.6 mg, 0.1 mmol), DIEA (0.026 mL, 0.15 mmol), and HATU (45.6 mg, 0.12 mmol). The reaction mixture was stirred overnight and then 0.5 mL of DMSO was added to the mixture. The compound was then subjected to purification by prep LCMS to yield N-{cis-4-[(4-methylquinolin-2-yl)amino]cyclohexyl}-2-[4-(trifluoromethoxy)phenoxy]-acetamide trifluoroacetate (22.3 mg, 38%) as a white solid. ESI MS m/e 474.4 M + H+; 1H NMR (400 MHz, DMSO-d6) delta 12.47 (s, 1 H), 9.25 (s, 1 H), 8.00-7.92 (m, 3 H), 7.80 (t, J = 7.2 Hz, 1 H), 7.53 (t, J = 8.0 Hz, 1 H), 7.31 (d, J = 8.8 Hz, 2 H), 7.04-7.01 (m, 3 H), 4.55 (s, 2 H), 4.06 (m, 1 H), 3.84 (m, 1 H), 2.69 (s, 3 H), 1.78-1.68 (m, 8 H).

References: [1]Patent: EP1464335,2004,A2 .Location in patent: Page/Page column 294.

6
[ 2731-16-0 ]
[ 72220-50-9 ]
N-deacetyl-N-(4-trifluoromethoxyphenoxyacetyl)thiocolchicine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 20h;	The reaction mixture of N-deacetylthiocolchicine (15 mg., 0.04 mmol), <strong>[72220-50-9]4-trifluoromethoxyphenoxyacetic acid</strong> (18 mg., 0.08 mmol), EDCI (25 mg, 0.13 mmol), DMAP (2 mg, 0.02 mmol) and dichloromethane (3 ml) was stirred at room temperature for 20 h. Then dichloromethane (20 ml) was added. Organic layer was washed with H2O, 5% Na2CO3 and brine, and then dried over MgSO4. After the solvent was removed under vaccum, the residue was separated by column chromatography (eluent: ethyl acetate and petroleum ether) to afford 17.9 mg N-Deacetyl-N-(4-trifluoromethosyphenoxyacetyl)thiocolchicine, mp 90-92 C. [0459] The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz): delta 7.29 (d, 1H, Ar-H), 7.22 (s, 1H, Ar-H), 7.18 (m, 3H, Ar-H and NH), 7.06 (d, 1H, H12), 6.94 (d, 1H, H11), 6.55 (s, 1H, H4), 4.73 (m, 1H, H7), 4.42 (q, 2H, COCH2O), 3.95 (s, 3H, OCH3), 3.91 (s, 311, OCH3), 3.68 (s, 3H, OCH3), 2.43 (s, 3H, SCH3), 2.60-1.80 (m, 4H, H5,6).

References: [1]Patent: US2004/204370,2004,A1 .Location in patent: Page/Page column 17.

7
[ 867340-08-7 ]
[ 72220-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; for 3h;	Example 2; [0213] (4-Trifluoromethoxyphenoxy)-acetic acid: TFA (80 mL) was added to (4- trifluoromethoxyphenoxy) -acetic acid tert-butyl ester (25.8 g, 88 mmol). The mixture was stirred for three hours. The TFA was removed in vacuo affording the title compound as a white solid: MS (ESI-LCMS) for C9H6F304: 235 (M-H-).

References: [1]Patent: WO2005/97765,2005,A1 .Location in patent: Page/Page column 273.

8
[ 710328-51-1 ]
[ 72220-50-9 ]
N-[4-methyl-2-(4-pyrrolidin-1-yl-piperidin-1-yl)-quinazolin-6-yl]-2-(4-trifluoromethoxy-phenoxy)-acetamide [ No CAS ]