924869-17-0|Methyl benzo[d]oxazole-5-carboxylate| Ambeed

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Quality Control of [ 924869-17-0 ] Purity: 97% SDS Specification

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Product Details of [ 924869-17-0 ]

CAS No. :	924869-17-0
Formula :	C₉H₇NO₃
M.W :	177.16
SMILES Code :	COC(=O)C1=CC2=C(OC=N2)C=C1
MDL No. :	MFCD08689687
InChI Key :	VHLBJWCXFIGALN-UHFFFAOYSA-N
Pubchem ID :	589828

Safety of [ 924869-17-0 ]

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

Computational Chemistry of [ 924869-17-0 ] 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.	2.03
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)	2.05

Application In Synthesis of [ 924869-17-0 ]

* 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 [ 924869-17-0 ]

[ 924869-17-0 ] Synthesis Path-Downstream 1~38

1
3-formylamino-4-hydroxy-benzoic acid methyl ester [ No CAS ]
[ 924869-17-0 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1915,vol. <2> 92,p. 265.

2
[ 536-25-4 ]
[ 924869-17-0 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1915,vol. <2> 92,p. 265.

3
[ 64-18-6 ]
[ 536-25-4 ]
[ 924869-17-0 ]

References: [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1187 - 1190.

4
[ 924869-17-0 ]
[ 106-49-0 ]
[ 1048974-16-8 ]

References: [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1187 - 1190.

5
[ 924869-17-0 ]
[ 106-47-8 ]
[ 1048974-22-6 ]

References: [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1187 - 1190.

6
[ 924869-17-0 ]
[ 104-94-9 ]
[ 1048974-19-1 ]

References: [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1187 - 1190.

7
[ 924869-17-0 ]
[ 100-01-6 ]
[ 1048974-25-9 ]

References: [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1187 - 1190.

8
[ 924869-17-0 ]
[ 62-53-3 ]
[ 1048974-14-6 ]

References: [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1187 - 1190.

9
[ 924869-17-0 ]
[ 124-38-9 ]
[ 1227406-85-0 ]

References: [1]Organic Letters,2010,vol. 12,p. 3567 - 3569.

10
[ 924869-17-0 ]
[ 124-38-9 ]
[ 74-88-4 ]
[ 1236115-21-1 ]

References: [1]Organic Letters,2010,vol. 12,p. 3567 - 3569.

11
[ 122-51-0 ]
[ 536-25-4 ]
[ 924869-17-0 ]

References: [1]Organic Letters,2010,vol. 12,p. 3567 - 3569.

12
[ 924869-17-0 ]
[ 71-43-2 ]
[ 21095-63-6 ]

References: [1]Chemical Communications,2012,vol. 48,p. 8964 - 8966.

13
[ 924869-17-0 ]
[ 637-44-5 ]
methyl 2-(phenylethynyl)benzoxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); silver(l) oxide; In N,N-dimethyl-formamide; at 80℃;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), silver(I) oxide (229 mg, 1 mmol) and aryl propiolic acid (1 mmol), under air, were added. Azole substrate (0.5 mmol) in DMF (4 mL) was added to the reaction mixture. The reaction mixture was stirred at 80 C for 6-8 h. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice cold water and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

References: [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981.

14
[ 924869-17-0 ]
[ 536-74-3 ]
methyl 2-(phenylethynyl)benzoxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); caesium carbonate; silver(l) oxide; In N,N-dimethyl-formamide; at 85℃; for 8h;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), cesium carbonate (325 mg, 1 mmol), silver(I) oxide (229 mg, 1 mmol) and azole substrate (0.5 mmol) in 2 mL DMF, under air, were added. Phenyl acetylene substrate (1 mmol) in DMF (2 mL) was added to the reaction vessel slowly by dropping funnel over 2 h while stirring the reaction mixture on preheated oil bath at 85 C. The reaction was allowed to stir for 6 h at the same temperature. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice coldwater and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

References: [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981.

15
[ 924869-17-0 ]
[ 15310-02-8 ]
methyl 2-(2-benzamidophenyl)-1,3-benzoxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(l) iodide; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; for 20h;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.

16
[ 924869-17-0 ]
[ 106-41-2 ]
methyl 2-(4-hydroxyphenyl)benzo[d]oxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate; tricyclohexylphosphine; In toluene; at 160℃; for 0.5h;Microwave irradiation;	At 20 from Preparative Example 1The obtained methylbenzo [d] oxazole-5-carboxylate 354.1 mg (2.0 mmol) was dissolved in toluene (20 mL, 0.1 M)4-Bromophenol (380.6 mg, 2.2 mmol), Palladium acetate (Pd (OAc) 2, 4.5 mg, 1 mol%),Copper acetate monohydrate (Cu (OAc) 2 .H2O, 72.6 mg, 20 mol%),Tricyclohexylphosphine (PCy3, 280.4 mg, 50 mol%) And potassium carbonate (K2CO3, 552.8 mg, 4 mmol) were slowly added.The reaction mixture was reacted in a microwave at 160 C for 0.5 hour under a condition of 200W, The reaction was terminated by the addition of aqueous ammonium chloride solution, Ethyl acetate (10 mL) was extracted and extracted three times. After the water of the organic layer was removed with sodium sulfate,The solvent was concentrated with a vacuum distillation apparatus.The residue was purified by silica gel chromatography to give the title compoundMethyl 2- (4-hydroxyphenyl) benzo [d] oxazole-5-carboxylate(360.6 mg, 67%) was obtained

References: [1]Patent: KR101792743,2017,B1 .Location in patent: Paragraph 0192-0196.
[2]Journal of Natural Products,2019,vol. 82,p. 1325 - 1330.

17
[ 67-56-1 ]
[ 149-73-5 ]
[ 1571-72-8 ]
[ 924869-17-0 ]