[ CAS No. 87150-13-8 ] {[proInfo.proName]}

Name: 87150-13-8|4-(5-Oxazolyl)benzonitrile|97%
Brand: Ambeed
SKU: A560326
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Quality Control of [ 87150-13-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 87150-13-8 ]

SDS Specification

Alternatived Products of [ 87150-13-8 ]

Product Details of [ 87150-13-8 ]

CAS No. :	87150-13-8	MDL No. :	MFCD00084987
Formula :	C₁₀H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LZMCNLOQTURTHS-UHFFFAOYSA-N
M.W :	170.17	Pubchem ID :	2777271
Synonyms :

Calculated chemistry of [ 87150-13-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.65
TPSA :	49.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	1.72
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	2.4
Consensus Log Po/w :	1.72

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.54
Solubility :	0.492 mg/ml ; 0.00289 mol/l
Class :	Soluble
Log S (Ali) :	-2.38
Solubility :	0.706 mg/ml ; 0.00415 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.84
Solubility :	0.0248 mg/ml ; 0.000146 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 87150-13-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 87150-13-8 ]

* 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 [ 87150-13-8 ]

[ 87150-13-8 ] Synthesis Path-Downstream 1~59

1
[ 38622-91-2 ]
[ 105-07-7 ]
[ 87150-13-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In methanol; at 20℃; for 1.33333h;	4-(oxazol-5-yI)benzonitrile A mixture of 4-formylbenzonitrile (commercially available from for example Aldrich) (5.32 g, 41 mmol), l-((isocyanomethyl)sulfonyl)-4-methylbenzene (commercially available from for example Aldrich) (8.83 g, 45 mmol) and potassium carbonate (7.3 g, 53 mmol) in methanol (200 mL) was stirred at ambient temperature for 80 minutes. The mixture was then evaporated to dryness; the residue was treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with dichloromethane (3 x 100 mL). The combined organics were washed with brine (75 mL), passed through a hydrophobic frit and then evaporated to dryness to afford the title compound (7.19 g, 42 mmol, quantitative). LCMS RT= 0.48 min, ES+ve m/z 171 [M+H]+.
100%	With potassium carbonate; In methanol; at 20℃; for 1.33333h;	A mixture of 4-formylbenzonitrile (commercially available from for example Aldrich) (5.32 g, 41 mmol), 1-((isocyanomethyl)sulfonyl)-4-methylbenzene (commercially available from for example Aldrich) (8.83 g, 45 mmol) and potassium carbonate (7.3 g, 53 mmol) in methanol (200 mL) was stirred at ambient temperature for 80 minutes. The mixture was then evaporated to dryness; the residue was treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with dichloromethane (3×100 mL). The combined organics were washed with brine (75 mL), passed through a hydrophobic fit and then evaporated to dryness to afford the title compound (7.19 g, 42 mmol, quantitative). LCMS RT=0.48 min, ES+ve m/z 171 [M+H]+.
100%	With potassium carbonate; In methanol; at 20℃; for 1.33333h;	4- (Oxazol- 5-yl)benzonitrile A mixture of 4-formylbenzonitrile (commercially available from for example Aldrich) (5.32 g, 41 mmol), l-((isocyanomethyl)sulfonyl)-4-methylbenzene (commercially available from for example Aldrich) (8.83 g, 45 mmol) and potassium carbonate (7.3 g, 53 mmol) in methanol (200 mL) was stirred at ambient temperature for 80 minutes. The mixture was then evaporated to dryness; the residue was treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with dichloromethane (3 x 100 mL). The combined organics were washed with brine (75 mL), passed through a hydrophobic frit and then evaporated to dryness to afford the title compound (7.19 g, 42 mmol, quantitative). LCMS RT= 0. 75min, ES+ve m/z 171 [M+H]+.

97%	With potassium carbonate; In methanol; for 1h;Heating / reflux;	-Preparation of 4-Oxazol-5-yl-benzonitrile; To a solution of 4-Formyl-benzonitrile (5 g, 38.17 mmol) and tosylmethyl isocyanide (TosMIC) (from Aldrich, 8.33 g, 42 mmol) in MeOH (200 mL) was added K2CO3 (6.85 g, 49.62 mmol) and the mixture was stirred at reflux for Ih. The solvent was then evaporated and saturated aqueous NaHCC>3 was added. The resultant suspension was extracted with dichloromethane (3x100 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and concentrated to leave a yellow <n="9"/>solid. Trituration with heptane afforded a solid that was collected by filtration and dried under vacuum to give the title compound (6.3 g, 97%). m.p. = 1400C 1H NMR (DMSO-/) delta = 7.91-7.98 (5H, m), 8.58 (IH, s).
84%	With potassium carbonate; In methanol; for 1.5h;Reflux;	Compound 1: 4-(oxazol-5-yl)benzonitrile To a 500 mL round-bottom flask was added 4-cyanobenzaldehyde (5.00 g, 38.1 mmol), methanol (200 mL), p-toluene sulfonylmethyl isocyanide (8.33 g, 42.66 mmol), followed by potassium carbonate (6.85 g, 49.56 mmol). The reaction mixture was stirred at reflux for about 1.5 hour and followed by TLC. The solvent was then evaporated and saturated aq.NaHCO3 was added. The resultant suspension was extracted with CH2Cl2 (3*100 mL). Combined organic layers were washed with brine, dried (anhydrous Na2SO4), and concentrated to leave a yellow solid. Trituration with hexane afforded a solid which was collected by filtration and dried. Crude product was further purified by re-crystallization using hot-CH2Cl2 and cold-hexane to afford title compound 1 (5.48 g, 84% yield). MS (ES) m/z 171 (M+H+).
75%	With potassium carbonate; at 80℃; for 1.5h;	General procedure: To a solution of p-anisaldehyde (1.22 mL, 10.0 mmol) in MeOH (25 mL) were added K2CO3 (1.52 g, 11.0 mmol) and TosMIC (1.08 g, 5.50mmol). The reaction mixture was stirred for 1.5 h at 80 C, cooled down to rt, quenched with H2O, and diluted with EtOAc. After removal of the organic layer, the aqueous layer was extracted with EtOAc. The organic layer was combined, dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (3:1 hexanes/EtOAc) afforded 5-(4-methoxyphenyl)oxazole (1) (955 mg, 99%) as a pale yellow solid
1 g	With potassium carbonate; In methanol; at 20℃; for 1.5h;	Step 1: 1. Synthesis of 4-(l,3-oxazol-5-yl)benzonitrile (S) [0428] To a stirred solution of 4-formylbenzonitrile (R, 1.0 g, 7.63 mmol) in methanol(40 mL) was added [[(4-methylbenzene)sulfonyl]methyl](methyliumylidyne)azanuide (1.6 g, 8.40 mmol) and potassium carbonate (1.4 g, 9.91 mmol), the resulting mixture was stirred at rt for 1.5 h. The bulk of solvent was then removed under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate (20 mL) and was extracted with dichloromethane (30 mL x 3). The organic layers were combined, washed with brine (30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a crude product, which was purified by re-crystallization using dichloromethane and hexane to give S (1.0 g) as a white solid. 1H NMR (400 MHz, DMSO) delta 8.56 (s, 1H), 7.97-7.83 (m, 5H); LC-MS (ES+): m/z 170.95 [MH+], tR= 0.79 min (2.0 minute run).

Reference： [1]Patent: WO2013/106646,2013,A2 .Location in patent: Page/Page column 185-186
[2]Patent: US2014/356322,2014,A1 .Location in patent: Paragraph 0420
[3]Patent: WO2015/867,2015,A1 .Location in patent: Page/Page column 47
[4]Patent: WO2007/131953,2007,A1 .Location in patent: Page/Page column 7-8
[5]Zeitschrift fur Naturforschung, B: Chemical Sciences,2017,vol. 72,p. 923 - 926
[6]Patent: US2012/302578,2012,A1 .Location in patent: Page/Page column 20
[7]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 313 - 316
[8]Liebigs Annalen der Chemie,1984,p. 641 - 648
[9]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997
[10]Angewandte Chemie - International Edition,2013,vol. 52,p. 4457 - 4461
Angew. Chem.,2013,vol. 125,p. 4553 - 4557,5
[11]Journal of Organic Chemistry,2013,vol. 78,p. 11045 - 11052
[12]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 23 - 28
[13]Journal of Medicinal Chemistry,2014,vol. 57,p. 8657 - 8663
[14]Patent: WO2016/118666,2016,A1 .Location in patent: Paragraph 0426; 0427; 0428

2
[ 105-07-7 ]
PS-TosMIC resin [ No CAS ]
[ 87150-13-8 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 5633 - 5636

3
[ 29166-72-1 ]
[ 105-07-7 ]
[ 87150-13-8 ]

Reference： [1]Organic Letters,2001,vol. 3,p. 271 - 273

4
[ 87150-13-8 ]
4-(2-chloro-oxazol-5-yl)-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		Compound 2: 4-(2-chlorooxazol-5-yl)benzonitrile LiHMDS (1.06 M in THF, 21.0 mL, 21.15 mmol) was added to a solution of 1 (3.00 g, 17.64 mmol) in THF (100 mL) at -78 C., and the mixture was stirred at -78 C. for 1 h. A solution of hexachloroethane (6.27 g, 26.48 mmol) in THF (9 mL) was added at -78 C., and the mixture was stirred at -78 C. for 2 h and allowed to warm to room temperature and stirred for 14 h. The reaction was quenched by adding EtOAc:H2O (50 mL:15 mL), and then extracted with ethyl acetate. The extracts were washed with brine, dried (Na2SO4) and concentrated. The product was purified by column chromatography (Acetone/hexane as an eluent) to provide 2 (3.15 g, 88% yield) as white solid. MS (ES) m/z 205 (M+H+).
82%		-Preparation of4-(2-Chloro-oxazol-5-yl)-benzonitrile; To a solution of 4-Oxazol-5-yl-benzonitrile (3 g, 17.65 mmol) in anhydrous THF (80 mL) at -78 0C under an argon atmosphere was slowly added a solution of LiHMDS (21.2 mL, 1 M in THF, 21.2 mmol). After Ih at -78 0C, solid hexachloroethane (6.275 g, 26.48 mmol) was added. The mixture was then stirred at -78 0C for Ih and allowed to slowly warm to room temperature and stir for 3 h. The reaction was diluted with AcOEt/H2O (50 mL/15 mL). The organic layer was washed with brine, dried with MgSO4 and filtered. After removal of solvent the solid obtained was recrystalize from Hexane to give the title compound as a white solid (2.95 g, 82%). m.p. = 144C 1H NMR (DMSO-/) delta = 7.89 (d, J= 8.4, 2H); 7.97 (d, J= 8.4, 2H); 8.04 (s, IH).

Reference： [1]Patent: US2012/302578,2012,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2007/131953,2007,A1 .Location in patent: Page/Page column 8

5
[ 288-42-6 ]
[ 623-00-7 ]
[ 87150-13-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4748 - 4760
[2]Tetrahedron,2009,vol. 65,p. 6348 - 6353

6
[ 1186127-11-6 ]
[ 623-00-7 ]
[ 87150-13-8 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6348 - 6353

7
[ 623-00-7 ]
[ 433332-27-5 ]
[ 87150-13-8 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6348 - 6353

8
C₁₇H₁₄N₂O₃S [ No CAS ]
[ 87150-13-8 ]

Reference： [1]Letters in Organic Chemistry,2009,vol. 6,p. 293 - 296

9
[ 637-59-2 ]
[ 87150-13-8 ]
[ 1258619-27-0 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12307 - 12311

10
[ 87150-13-8 ]
[ 959977-83-4 ]

Reference： [1]Organic Syntheses,2010,vol. 87,p. 16 - 25
[2]Organic Process Research and Development,2007,vol. 11,p. 951 - 955

11
[ 4545-18-0 ]
[ 87150-13-8 ]
[ 1361974-16-4 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 775 - 779

12
[ 221044-05-9 ]
[ 87150-13-8 ]
[ 1402228-09-4 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997

13
[ 95-16-9 ]
[ 87150-13-8 ]
[ 4271-09-4 ]
[ 1395680-17-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 7677 - 7683

14
[ 87150-13-8 ]
[ 672324-91-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With ammonium hydroxide; hydrogen; In methanol; water; at 20℃; for 16h;	Step 2. Synthesis of [4-(l,3-oxazol-5-yl)phenyl]methanamine (T)[0430] To a stirred solution of 4-(l,3-oxazol-5-yl)benzonitrile (S, 900.0 mg, 5.29 mmol) in methanol (15 mL) was added Raney-Ni (900 mg) and aq. ammonium hydroxide (3.0 mL). Hydrogen gas was then introduced into the reaction mixture via a balloon. The resulting mixture was stirred at rt for 16 h. The solids were then removed by filtration and the solution was concentrated under vacuum to give T (yield: 81%) as brown oil, which was used in the next step without any further purifications. LC-MS (ES+): m/z 175.90 [MH+], tR= 0.26 min (2.0 minute run).
63%	With methanol; sodium tetrahydroborate; cobalt(II) chloride hexahydrate; for 0.5h;Inert atmosphere; Cooling with ice;	(4-(oxazol-5-yl)phenyl)methanamine Under an atmosphere of nitrogen, an ice-cooled mixture of <strong>[87150-13-8]4-(oxazol-5-yl)benzonitrile</strong> (900 mg, 5.29 mmol) and cobalt(II) chloride hexahydrate (commercially available from for example Aldrich) (1.8 g, 7.9 mmol) in methanol (50 mL) was treated portion- wise over 5 minutes with sodium borohydride (1 g, 26 mmol). The mixture was stirred for 30 minutes and then treated with water (50 mL) and concentrated aqueous ammonia (20 mL). The mixture was extracted with chloroform (3 x 150 mL), the combined organics were evaporated to dryness and the product was purified by chromatography on silica using a gradient elution from 0% to 30% methanol in dichloromethane (+ 0.1% triethylamine) to afford the title compound (580 mg, 3.3 mmol, 63 % yield). LCMS RT= 0.35 min, ES+ve m/z 175 [M+H]+.
63%	With methanol; sodium tetrahydroborate; cobalt(II) chloride hexahydrate; for 0.5h;Cooling;	Under an atmosphere of nitrogen, an ice-cooled mixture of <strong>[87150-13-8]4-(oxazol-5-yl)benzonitrile</strong> (900 mg, 5.29 mmol) and cobalt(II) chloride hexahydrate (commercially available from for example Aldrich) (1.8 g, 7.9 mmol) in methanol (50 mL) was treated portion-wise over 5 minutes with sodium borohydride (1 g, 26 mmol). The mixture was stirred for 30 minutes and then treated with water (50 mL) and concentrated aqueous ammonia (20 mL). The mixture was extracted with chloroform (3×150 mL), the combined organics were evaporated to dryness and the product was purified by chromatography on silica using a gradient elution from 0% to 30% methanol in dichloromethane (+0.1% triethylamine) to afford the title compound (580 mg, 3.3 mmol, 63% yield). LCMS RT=0.35 min, ES+ve m/z 175 [M+H]+.

63%	With methanol; sodium tetrahydroborate; cobalt(II) chloride hexahydrate; for 0.583333h;Inert atmosphere; Cooling with ice;	(4- (Oxazol- 5-yl)phenyl) methanamine Under an atmosphere of nitrogen, an ice-cooled mixture of <strong>[87150-13-8]4-(oxazol-5-yl)benzonitrile</strong> (900 mg, 5.29 mmol) and cobalt(II) chloride hexahydrate (commercially available from for example Aldrich) (1.8 g, 7.9 mmol) in methanol (50 mL) was treated portion-wise over 5 minutes with sodium borohydride (1 g, 26 mmol). The mixture was stirred for 30 minutes and then treated with water (50 mL) and concentrated aqueous ammonia (20 mL). The mixture was extracted with chloroform (3 x 150 mL), the combined organics were evaporated to dryness and the product was purified by chromatography on silica using a gradient elution from 0% to 30% methanol in dichloromethane (+ 0.1% triethylamine) to afford the title compound (580 mg, 3.3 mmol, 63 % yield). LCMS RT= 0.35 min, ES+ve m/z 175 [M+H]+.
	With hydrogen;palladium on activated charcoal; In methanol; for 14h;	Compound 10: (4-(oxazol-5-yl)phenyl)methanamine<strong>[87150-13-8]4-(oxazol-5-yl)benzonitrile</strong> 1 (1.50 g, 8.82 mmol) was dissolved in methanol (20 mL) treated with H2 (balloon pressure) for 14 h in the presence of Pd/C (catalytic, 150 mg). The reaction was monitored by TLC until the starting material was no longer detected. The Pd/C residue was removed by filtration over celite pad, followed by rotary evaporation of the solvent obtained 1.34 g of 10 (88% yield). The crude product was further used without further purification. MS (ES) m/z 175 (M+H+).

Reference： [1]Patent: WO2016/118666,2016,A1 .Location in patent: Paragraph 0426; 0429; 0430
[2]Patent: WO2013/106646,2013,A2 .Location in patent: Page/Page column 186
[3]Patent: US2014/356322,2014,A1 .Location in patent: Paragraph 0421
[4]Patent: WO2015/867,2015,A1 .Location in patent: Page/Page column 47-48
[5]Patent: US2012/302578,2012,A1 .Location in patent: Page/Page column 22
[6]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 23 - 28
[7]Journal of Medicinal Chemistry,2014,vol. 57,p. 8657 - 8663

15
[ 87150-13-8 ]
[ 1105712-04-6 ]