1086378-35-9|Methyl benzo[d]oxazole-7-carboxylate| Ambeed

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Quality Control of [ 1086378-35-9 ] Purity: 95% SDS Specification

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Product Details of [ 1086378-35-9 ]

CAS No. :	1086378-35-9
Formula :	C₉H₇NO₃
M.W :	177.16
SMILES Code :	COC(=O)C1=CC=CC2=C1OC=N2
MDL No. :	MFCD11042246
InChI Key :	SVWYSYMOKICPBK-UHFFFAOYSA-N
Pubchem ID :	19771047

Safety of [ 1086378-35-9 ]

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

Computational Chemistry of [ 1086378-35-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.11
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	45.29
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.33 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.02
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	1.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.61
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.	0.9
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	1.71
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.34
Solubility	0.811 mg/ml ; 0.00458 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.	-2.33
Solubility	0.826 mg/ml ; 0.00466 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	-2.99
Solubility	0.182 mg/ml ; 0.00103 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.	-6.23 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	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)	2.19

Application In Synthesis of [ 1086378-35-9 ]

* 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 [ 1086378-35-9 ]

[ 1086378-35-9 ] Synthesis Path-Downstream 1~28

Yield	Reaction Conditions	Operation in experiment
98.2%	With toluene-4-sulfonic acid; for 0.5h;Inert atmosphere; Reflux;	General procedure: The compound obtained in Example 32-1 (400 mg, 3.20 mmol) triethyl orthoformate (3.2 ml, 19.2 mmol) in solution,para-tosylic acid monohydrate(30 mg, 0.16 mmol) was added dropwise. Under an argon atmosphere, followed by stirring for 30 minutes under reflux conditions, it was solidified after completion of the reaction concentrated to dryness. The residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (232 mg, 54%)
		Example XV Methyl 2-benzoxazole-7-carboxylate STR34 5.8 ml of CCl4 in 5 ml of acetonitrile were added to 30 mmol of the compound from Example XIV, 30 mmol of benzoic acid, 50 mmol of triphenylphosphine and 120 mmol of triethylamine in 100 ml of acetonitrile at 3 C. under argon in the course of 15 min and the mixture was stirred at room temperature for 20 hours and concentrated, diethyl ether was added to the residue, the solid was filtered off with suction, the filtrate was concentrated and the residue was separated on silica gel. M.p.: 77 C. (white needles)

2
[ 1086378-35-9 ]
[ 15310-02-8 ]
methyl 2-(2-benzamidophenyl)-1,3-benzoxazole-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(l) iodide; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; for 20.0h;Inert atmosphere; Reflux;	General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 1374 - 1377.

3
[ 35748-34-6 ]
[ 122-51-0 ]
[ 1086378-35-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With ytterbium(III) triflate; In toluene; at 100℃; for 1.0h;Microwave irradiation;	Methyl 3-amino-2-hydroxybenzoate (1.69 g, 10.13 mmol) was suspended in toluene (2 mL) in a microwave vial. HC(OEt)3 (1.80 g, 12.15 mmol) and Yb(OTf)3 (0.003 g, 0.005 mmol) was added and the reaction was heated at 100 C for 1 hour in the microwave. The reaction mixture was evaporated and purified by flash chromatography (petroleum ether/EtOAc 4:1) to give the title compound (1.63 g, 91%) as pale yellow crystals. mp. 116 - 118 C (Litt9. 77 C). 1H NMR (300 MHz, CDCl3) delta 8.21 (s, 1H), 8.04 (dd, J = 7.8, 1.2 Hz, 1H), 7.99 (dd, J = 8.0, 1.2 Hz, 1H), 7.44 (dd, J = 8.0, 7.8 Hz), 3.76 (s, 3H). 13C NMR (75 MHz, CDCl3) delta 180.9, 164.4, 153.4, 141.4, 128.0, 125.6, 124.5, 115.4, 52.6

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937.

4
[ 85-38-1 ]
[ 1086378-35-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937.

5
[ 22621-41-6 ]
[ 1086378-35-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937.

6
[ 1086378-35-9 ]
C₁₈H₁₇BrN₂O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937.

7
[ 1086378-35-9 ]
benzo[d]oxazole-7-yl methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 0.5h;	Methyl benzo[d]oxazole-7-carboxylate (1.57 g, 8.86 mmol) was dissolved in dry THF (50 mL) and there was added a 1.0M solution of LiAlH4 in THF (5mL, 5 mmol). The reaction was stirred at room temperature for 30 minutes at which point TLC indicated full conversion. The reaction was quenched by addition of water (50 mL) and there was added saturated aqueous Rochelle salt (50 mL) and Et2O (50 mL). The reaction was stirred vigorously for 15 minutes and then transferred to a separatory funnel. The organic layer was isolate and the aqueous layer was extracted with Et2O (2 × 100 mL). The combined organic layers were washed with saturated aqueous Rochelle salt (50 mL) and water (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure. The crude compound was purified by flash chromatography (petroleum ether/EtOAc 3:1) to give the title compound (0.823 g, 62%) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 8.07 (s, 1H), 7.69 (dd, J = 7.7, 1.3 Hz, 1H), 7.40 (dd, J = 7.7, 1.3 Hz, 1H), 7.33 (t, J = 7.7 Hz), 5.00 (s, 2H), 2.51 (br s, 1H). 13C NMR (75 MHz, CDCl3) delta 153.4, 145.4, 140.0, 124.8, 124.7, 124.4, 119.9, 60.3
14.5%	With sodium tetrahydroborate; ethanol; calcium chloride; In tetrahydrofuran; at 20℃; for 2.0h;Cooling with ice;	The compound obtained in Example 51-2 (1.221 g, 6.89 mmol) and THF (24 ml), was dissolved in ethanol (24 ml), cooled with ice. Thereto calcium chloride (1.529 g, 13.78 mmol), sodium borohydride (1.043 g, 27.56 mmol) was stirred at room temperature for 2 hours added. After the reaction was extracted with ethyl acetate by adding 1 mol / l hydrochloric acid. It was washed with a saturated aqueous sodium bicarbonate solution. Dried with magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (SNAP ULTRA 25 g, hexane / ethyl acetate) to give the title compound (149 mg, 14.5%) as a white solid.

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937.
[2]Patent: JP2016/124812,2016,A .Location in patent: Paragraph 0142.

8
[ 1086378-35-9 ]
benzo[d]oxazole-7-carbaldehyde [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3933 - 3937.

9
[ 1086378-35-9 ]
7-(((tert-butyldimethylsilyl)oxy)methyl)benzo[d]oxazole [ No CAS ]

References: [1]Patent: JP2016/124812,2016,A .

10
[ 1086378-35-9 ]
[ 75-16-1 ]
2-(benzo[d]oxazol-7-yl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	In tetrahydrofuran; 2-methyltetrahydrofuran; at 0 - 20℃;	A solution of <strong>[1086378-35-9]methyl benzo[d]oxazole-7-carboxylate</strong> (300 mg, 1.7 mmol) in THF (5 mL) was cooled down to 0C and methyl magnesium bromide 3.2M in 2-Me-THF (3.0 equiv., 5.1 mmol) was added dropwise. The mixture was allowed to warm-up to room temperature and quenched with saturated solution of NH4Cl. The resulting mixture was extracted 3 times with EtOAc and the organic solutions were washed with brine, dried with Na2SO4 and concentrated to dryness. The crude was purified by column chromatography on silica gel using DCM:EtOAc (95:5) as mobile phase to give 2-(benzo[d]oxazol-7-yl)propan-2-ol (110 mg, 37%). UPLC-MS (Acidic Method, 2 min): rt 0.78 min, m/z 178.0 [M+H]+

References: [1]Patent: WO2020/43880,2020,A1 .Location in patent: Page/Page column 32; 33.

11
[ 1086378-35-9 ]
^m^{ethyl 2-(4-aminophenyl)benzo[d]oxazole-7-carboxylate} [ No CAS ]