[ CAS No. 17153-21-8 ] {[proInfo.proName]}

Name: 17153-21-8|3-Methyl-5-phenylisoxazole-4-carboxylic acid|97%
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SKU: A131385
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Quality Control of [ 17153-21-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17153-21-8 ]

SDS Specification

Alternatived Products of [ 17153-21-8 ]

Product Details of [ 17153-21-8 ]

CAS No. :	17153-21-8	MDL No. :	MFCD03086120
Formula :	C₁₁H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GLNQCTGGLIXRRJ-UHFFFAOYSA-N
M.W :	203.19	Pubchem ID :	2776514
Synonyms :

Calculated chemistry of [ 17153-21-8 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.09
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.86
TPSA :	63.33 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) :	-6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.7
Log Po/w (XLOGP3) :	1.96
Log Po/w (WLOGP) :	2.35
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	2.25
Consensus Log Po/w :	1.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.75
Solubility :	0.365 mg/ml ; 0.0018 mol/l
Class :	Soluble
Log S (Ali) :	-2.92
Solubility :	0.247 mg/ml ; 0.00122 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.52
Solubility :	0.0611 mg/ml ; 0.000301 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.8

Safety of [ 17153-21-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 17153-21-8 ]

* 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.

Upstream synthesis route of [ 17153-21-8 ]
Downstream synthetic route of [ 17153-21-8 ]

[ 17153-21-8 ] Synthesis Path-Upstream 1~7

1
[ 92029-29-3 ]
[ 17153-21-8 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2144 - 2153
[2] Gazzetta Chimica Italiana, 1915, vol. 45 I, p. 466
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 147 - 151

2
[ 569-37-9 ]
[ 17153-21-8 ]

Reference： [1] Gazzetta Chimica Italiana, 1915, vol. 45 I, p. 466
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2144 - 2153
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 147 - 151

3
[ 98-88-4 ]
[ 17153-21-8 ]

Reference： [1] Chemische Berichte, 1909, vol. 42, p. 3919
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2144 - 2153
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 147 - 151

4
[ 79-24-3 ]
[ 53256-23-8 ]
[ 17153-21-8 ]

Reference： [1] Journal of the American Chemical Society, 1967, vol. 89, p. 5461 - 5462

5
[ 112532-09-9 ]
[ 17153-21-8 ]

Reference： [1] Gazzetta Chimica Italiana, 1953, vol. 83, p. 192,209
[2] Gazzetta Chimica Italiana, 1953, vol. 83, p. 192,209

6
[ 82140-46-3 ]
[ 17153-21-8 ]

Reference： [1] Chemische Berichte, 1909, vol. 42, p. 3919

7
[ 93-97-0 ]
[ 1517-96-0 ]
[ 17153-21-8 ]

Reference： [1] Journal of Organic Chemistry, 1962, vol. 27, p. 4305 - 4309

[ 17153-21-8 ] Synthesis Path-Downstream 1~45

1
[ 82140-46-3 ]
[ 17153-21-8 ]

Reference： [1]Chemische Berichte,1909,vol. 42,p. 3919

2
4-(α-methoxy-benzylidene)-3-methyl-4<i>H</i>-isoxazol-5-one [ No CAS ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1953,vol. 83,p. 192,209

3
[ 17153-21-8 ]
[ 1008-75-9 ]

Reference： [1]Gazzetta Chimica Italiana,1915,vol. 45 I,p. 466
[2]Gazzetta Chimica Italiana,1963,vol. 93,p. 1714 - 1725

4
[ 17153-21-8 ]
[ 91182-77-3 ]

Reference： [1]Gazzetta Chimica Italiana,1921,vol. 51 II,p. 236

5
[ 92029-29-3 ]
[ 17153-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 3h;	General procedure: The mixture of ethyl acetoacetate (638 muL, 5 mmol), anhydrous magnesium chloride (571 mg, 6 mmol) and anhydrous pyridine (884 muL) in dry DCM (10 mL) was placed at 0. After stirring at 0for 30 min, the 4-chlorobenzoyl chloride (700 muL, 5.5 mmol) in dry DCM (1 mL) was added dropwise to the above solution. After the reaction was warm to room temperature and stirred for 3 h. The mixture was quenched with 6 mol/L HCl, washed with water, saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure to get the white oil. The mixture of oil and hydroxylamine hydrochloride (3.5 g, 50 mmol) in ethanol (10 mL) and water (1 mL) was refluxed for 5 h and concentrated under reduced pressure. The residue was dissolved with DCM (20 mL), washed with water, saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and concentrated under reduced pressure to get the brown solid (1.3 g). Sodium hydroxide (392 mg, 9.8 mmol) in water (15 mL) was added the solution of brown solid (1.3 g, 4.9 mmol) in methanol (5 mL) and THF (5 mL). After stirred for 3 h at room temperature, the solvent was removed under reduced pressure and the amount of water was added. The solution was washed with DCM and ethyl acetate. The aqueous phases wasacidified using a solution of HCl and filtered to get the white solid8a(1.11 g, 95.7%).Mp: 151-153.ESI-MS:m/z236 [M-H]-. The mixture of4(300 mg, 1.56 mmol),8a(470 mg, 1.88 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimidehydrochloride (820 mg, 3.76 mmol) and 4-dimethylaminopyridine (220 mg, 2.25 mmol) in dry DCM (10 mL) was stirred for 10 h at room temperature. The reaction solution was washed with HCl and brine and concentrated under reduced pressure. The residue was further purified by silica gel column (petroleum ether/ethyl acetate = 5:1) to yield pure compound9a(418 mg, 65.3%) as a white solid.

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2144 - 2153
[2]Gazzetta Chimica Italiana,1915,vol. 45 I,p. 466
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 147 - 151

6
[ 79-24-3 ]
[ 53256-23-8 ]
[ 17153-21-8 ]

Reference： [1]Journal of the American Chemical Society,1967,vol. 89,p. 5461 - 5462

7
[ 93-97-0 ]
[ 1517-96-0 ]
[ 17153-21-8 ]

Reference： [1]Journal of Organic Chemistry,1962,vol. 27,p. 4305 - 4309

8
[ 17153-21-8 ]
[ 113826-87-2 ]

Reference： [1]Synthesis,1990,p. 62 - 64

10
[ 7647-01-0 ]
[ 17153-21-8 ]
[ 1008-75-9 ]

Reference： [1]Gazzetta Chimica Italiana,1915,vol. 45 I,p. 466

12
3-methyl-5-phenyl-isoxazole-4-carboxylic acid amide [ No CAS ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1921,vol. 51 II,p. 237

13
3-methyl-5-phenyl-isoxazole-carboxylic acid-⁽⁴⁾ [ No CAS ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1915,vol. 45 I,p. 466

14
lower-melting form [ No CAS ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1921,vol. 51 II,p. 230,236

15
[ 936-44-7 ]
[ 17153-21-8 ]
3-methyl-5-phenyl-4-[(3-phenylpyrrolidin-1-yl)carbonyl]isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	3-Methyl-5-phenyl-4-isoxazolecarboxylic acid (40 mg, 0.197 mmol), <strong>[936-44-7]3-phenyl-pyrrolidine</strong> (31.6 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H20N2O2: 332.1525, found 332.1535.

Reference： [1]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 85

16
[ 106366-28-3 ]
[ 17153-21-8 ]
3-({1-[(3-methyl-5-phenylisoxazol-4-yl)carbonyl]pyrrolidin-2-yl}methyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	<strong>[17153-21-8]3-Methyl-5-phenyl-4-isoxazolecarboxylic acid</strong> (40 mg, 0.197 mmol), 3-(pyrrolidin-2-ylmethyl)pyridine (50.5 mg, 0.215 mmol), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (86.2 mg, 0.268 mmol) and diisopropylethylamine (25.4 mg, 0.197 mmol) were mixed in dimethylformamide (1.0 mL) and stirred at room temperature. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C21H21N3O2: 347.1634, found 347.1642.

Reference： [1]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 85-86

17
[ 17153-21-8 ]
[ 89479-66-3 ]

Reference： [1]Synthesis,1990,p. 62 - 64

18
4-benzoyl-3-methyl-2<i>H</i>-isoxazol-5-one [ No CAS ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1953,vol. 83,p. 192,209
[2]Gazzetta Chimica Italiana,1953,vol. 83,p. 192,209

19
[ 112532-09-9 ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1953,vol. 83,p. 192,209
[2]Gazzetta Chimica Italiana,1953,vol. 83,p. 192,209

20
[ 569-37-9 ]
[ 17153-21-8 ]

Reference： [1]Gazzetta Chimica Italiana,1915,vol. 45 I,p. 466
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 2144 - 2153
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 147 - 151

21
[ 98-88-4 ]
[ 17153-21-8 ]

Reference： [1]Chemische Berichte,1909,vol. 42,p. 3919
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 2144 - 2153
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 147 - 151

22
[ 74-89-5 ]
[ 17153-21-8 ]
5-methyl-3-phenyl-isoxazole-4-carboxylic acid methylamide [ No CAS ]

Reference： [1]Patent: JP2005/501847,2005,A .Location in patent: Page/Page column 12

23
[ 114878-60-3 ]
[ 17153-21-8 ]
[ 1362020-25-4 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2144 - 2153

24
3-amino-6-methoxy-7-(2-morpholinoethoxy)-2H-chromen-2-one [ No CAS ]
[ 17153-21-8 ]
N-[6-methoxy-7-(2-moropholinethoxy)-2-oxo-2H-chromen-3-yl]-3-methyl-5-phenylisoxazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.4%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 10h;	General procedure: The mixture of17(320 mg, 1 mmol),8a(284 mg, 1.2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (299 mg, 1.44 mmol) and 4-dimethylaminopyridine (117 mg, 1.2 mmol) in dry DCM (10 mL) was stirred at room temperature for 10 h. The reaction solution was washed with HCl and brine and concentrated under reduced pressure. The residue was further purified by silica gel column (petroleum ether/ethyl acetate = 1:2) to yield pure compound18a(396 mg, 73.6%) as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 147 - 151

25
[ 92-61-5 ]
[ 17153-21-8 ]
6-methoxy-2-oxo-2H-chromen-7-yl 3-methyl-5-phenylisoxazole-4-carboxylate [ No CAS ]