1092400-82-2|3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid| Ambeed

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Quality Control of [ 1092400-82-2 ] Purity: 98% SDS Specification

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Product Details of [ 1092400-82-2 ]

CAS No. :	1092400-82-2
Formula :	C₁₀H₅F₃N₂O₃
M.W :	258.15
SMILES Code :	O=C(O)C1=CC=CC(C2=NOC(C(F)(F)F)=N2)=C1
MDL No. :	MFCD09907879
InChI Key :	ZTOAUVQUTVRHBJ-UHFFFAOYSA-N
Pubchem ID :	25180854

Safety of [ 1092400-82-2 ]

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

Computational Chemistry of [ 1092400-82-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	11
Fraction Csp3	0.1
Num. rotatable bonds	3
Num. H-bond acceptors	8.0
Num. H-bond donors	1.0
Molar Refractivity	51.7
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	76.22 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.84
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	2.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.61
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.	1.99
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	2.27
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.11
Solubility	0.199 mg/ml ; 0.000772 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.	-3.49
Solubility	0.0842 mg/ml ; 0.000326 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	-3.65
Solubility	0.0582 mg/ml ; 0.000225 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.	-6.28 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<0.0
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)	2.46

Application In Synthesis of [ 1092400-82-2 ]

* 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 [ 1092400-82-2 ]

[ 1092400-82-2 ] Synthesis Path-Downstream 1~27

1
[ 407-25-0 ]
(Z)-3-(N'–hydroxycarbamimidoyl)benzoic acid [ No CAS ]
[ 1092400-82-2 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7843 - 7854.
[2]ChemMedChem,2019,vol. 14,p. 1096 - 1107.

2
[ 1092400-82-2 ]
[ 22483-09-6 ]
N-(2,2-dimethoxyethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	N-(2,2-Di methoxyethyl)-3-(5-(trifl uoromethyl)-1 ,2,4-oxadiazol-3-yI)benzamide 3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (8.3 g, 32.2 mmol), EDCI (hg, 57.2 mmol), HOBt (7.8 g, 57.2 mmol), and DIPEA (14.7 g, 114.3mmol) were added to a solution of 2,2-dimethoxyethanamine (3g 28.6mmol) in DCM (8OmL). The reaction mixture was stirred at room temperature overnight. Water (80 mL) was added to the mixture and the organic phase was separated. The aqueous phase was extracted withCH2CI2 (80 mL x3). The combined organic solvents were washed with brine (100 mL), dried over Na2504. After removal of solvents, the crude compound was purified by flash column (PE: EtOAc = 3:1) to provide N-(2,2-dimethoxyethyl)-3-(5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl)benzamide (6.2 g, yield 62%) as a yellow solid.

References: [1]Patent: WO2013/6408,2013,A1 .Location in patent: Page/Page column 58.

3
[ 1092400-82-2 ]
6-((3-aminopropyl)(methyl)amino)nicotinonitrile trifluoroacetic acid salt [ No CAS ]
N-(3-((5-cyanopyridin-2-yl)(methyl)amino)propyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With 4-methyl-morpholine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 4h;	3-(5-(Trifluoromethyl)-1 ,2,4-oxad iazol-3-yl)benzoic acid (75 mg, 0.29 m mol) was dissolved in dry DMF (5 mL), and HATU (130 mg, 0.34 mmol) followed by 6-((3- aminopropyl)(methyl)amino)nicotinonitrile TFA salt (176 mg, 0.58 mmol), and NMM (0.15 mL, 1.45 mmol) were added at 0 C. The reaction mixture was slowly warmed to roomtemperature and stirred for 4 h. The reaction mixture was then diluted with EtOAc, and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-1 20 mesh, eluant 40% EtOAc in petroleum ether) to get N-(3- ((5-cyanopyridin-2-yl)(methyl )ami no)propyl )-3-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzamide (50 mg, yield 41%) as an off-white solid. yl). 1H NMR (400 MHz, CDCI3) 6 8.58-8.55(m, 2H), 8.31 (d, J= 7.6 Hz, 1H), 8.17 (d, J= 7.6 Hz, 1H), 7.86 (brs, 1H), 7.71-7.66 (m, 2H), 6.59 (d, J = 9.2 Hz, 1 H), 3.91 - 3.88 (t, J = 6.0 Hz, 2H), 3.50 - 3.46 (q, J =6.0 Hz, 2H), 3.10 (s, 3H), 1.99-1.93 (m, 2H). MS (ESI) m/z: Calculated forC20H17F3N602: 430.14; found: 431.2 (M+H).

References: [1]Patent: WO2013/6408,2013,A1 .Location in patent: Page/Page column 42.

4
[ 199447-10-4 ]
[ 407-25-0 ]
[ 1092400-82-2 ]

Yield	Reaction Conditions	Operation in experiment
28%	With pyridine; at 0 - 50℃; for 3h;	3-(5-(Trifluoromethyl)-1 ,2,4-oxadiazol-3-yI)benzoic acidA solution of compound 3-(W-hydroxycarbamimidoyl)benzoic acid (1 g, 5.6 mmol) in anhydrous pyridine (15 mL) was cooled to 0 C and trifluoroacetic anhydride (2.3 mL, 16.7 mmol) was added dropwise. The reaction mixture was slowly warmed to roomtemperature and further heated to 50 C for 3 h. The reaction mixture was poured into ice- water and adjusted to pH -4 by addition of 1 .5N HCI. The product was extracted with EtOAc and the solvent removed under reduced pressure. The crude product was purified by column chromatography [silica gel 60-1 20 mesh, eluent: 10% EtOAc in petroleumether] to afford 3-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid (400mg, yield28%): 1H NMR (400 MHz, CDCI3) 6 13.44 (br s, 1H), 8.56 (s, 1H), 8.30 (d, J = 7.9 Hz, 1 H), 8.21 (d, J = 7.9 Hz, 1 H), 7.78 (t, J = 7.8 Hz, 1 H). MS (ESI) m/z: Calculated for C10H5F3N203: 258.03; found: 257 (M-H).
28%	In pyridine; at 0 - 50℃; for 3h;	A solution of compound 3-(N'-hydroxycarbamimidoyl)benzoic acid (1 g, 5.6 mmol) in anhydrous pyridine (15 mL) was cooled to 0 C and trifluoroacetic anhydride (2.3 mL, 16.7 mmol) was added dropwise. The reaction mixture was slowly warmed to room temperature and further heated to 50 C for 3 h. The reaction mixture was poured into ice-water and adjusted to pH ?4 by addition of 1.5N HCl. The product was extracted with EtOAc and the solvent removed under reduced pressure. The crude product was purified by column chromatography [silica gel 60-120 mesh, eluent: 10% EtOAc in petroleum ether] to afford 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (400mg, yield 28%): 1H NMR (400 MHz, CDCl3) delta 13.44 (br s, 1 H), 8.56 (s, 1 H), 8.30 (d, J = 7.9 Hz, 1 H), 8.21 (d, J = 7.9 Hz, 1 H), 7.78 (t, J = 7.8 Hz, 1 H). MS (ESI) m/z: Calculated for C10H5F3N2O3: 258.03; found: 257 (M-H)-.
28%	With pyridine; at 0 - 50℃; for 3h;	3-(5-(Trifluoromethyl)-l,2,4-oxadiazol-3-yl)benzoic acid (0797) (0798) A solution of compound 3-(N-hydroxycarbamimidoyl)benzoic acid (1 g, 5.6 mmol) in anhydrous pyridine (15 mL) was cooled to 0 C and trifluoroacetic anhydride (2.3 mL, 16.7 mmol) was added drop wise. The reaction mixture was slowly warmed to room temperature and further heated to 50 C for 3 h. The reaction mixture was poured into ice- water and adjusted to pH ~4 by addition of 1.5N HC1. The product was extracted with EtOAc and the solvent removed under reduced pressure. The crude product was purified by column chromatography [silica gel 60-120 mesh, eluent: 10% EtOAc in petroleum ether] to afford 3-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)benzoic acid (400mg, yield 28%): NMR (400 MHz, CDCh) delta 13.44 (br s, 1H), 8.56 (s, 1H), 8.30 (d, J= 7.9 Hz, 1H), 8.21 (d, J= 7.9 Hz, 1H), 7.78 (t, J= 7.8 Hz, 1H). LCMS-B (ESI) m/z: Calculated for C10H5F3N2O3: 258.03; found: 257 (M-H)".

References: [1]Patent: WO2013/6408,2013,A1 .Location in patent: Page/Page column 39; 40.
[2]Patent: EP2533783,2015,B1 .Location in patent: Paragraph 0136-0137.
[3]Patent: WO2017/112838,2017,A1 .Location in patent: Paragraph 87.

5
[ 1092400-82-2 ]
[ 121492-06-6 ]
tert-butyl methyl-(2-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamido)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;	tert-Butyl methyl(2-(3-(5-(trifluoromethyl)-1 ,2,4-oxadiazol -3- yI)benzamido)ethyl)carbamate 3-(5-(Trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid (1 .24 g, 4.8 mmol), EDCI(922 mg, 4.8 mmol), HOBt (648 mg, 4.8 mmol), and DIPEA (774 mg, 6mmol) were added to a solution of crude tert-butyl (2-aminoethyl)(methyl)carbamate in DCM (5OmL). The reaction mixture was stirred at room temperature overnight. Water (20 mL) was added to the mixture and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (40 mL x3). The combined organic solvents was washed with brine (30 mL), driedover Na2SO4. After removal of solvents, the crude compound was purified by flash column (EtOAc: PE = 2:1) to provide tert-butyl methyl(2-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamido)ethyl)carbamate as a white solid (1.1 g, yield 66%). MS (ESI) m/z: Calculated for C18H21F3N404: 414.15; found: 437 (M-f-Na).

References: [1]Patent: WO2013/6408,2013,A1 .Location in patent: Page/Page column 54.

6
[ 1877-72-1 ]
[ 1092400-82-2 ]

References: [1]Patent: WO2013/6408,2013,A1 .
[2]Patent: EP2533783,2015,B1 .
[3]Patent: WO2017/112838,2017,A1 .
[4]ChemMedChem,2019,vol. 14,p. 1096 - 1107.

7
[ 1092400-82-2 ]
N-(2-(methylamino)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide [ No CAS ]