[ CAS No. 13575-16-1 ] {[proInfo.proName]}

Name: 13575-16-1|Ethyl 5-phenyloxazole-2-carboxylate|98%
Brand: Ambeed
SKU: A149193
Price: 49.0 USD
Availability: InStock
Rating: 96 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 13575-16-1

Structure of 13575-16-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 13575-16-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13575-16-1 ]

SDS Specification

Alternatived Products of [ 13575-16-1 ]

Product Details of [ 13575-16-1 ]

CAS No. :	13575-16-1	MDL No. :	MFCD11975682
Formula :	C₁₂H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LRQAQFQUJNFEDT-UHFFFAOYSA-N
M.W :	217.22	Pubchem ID :	13388477
Synonyms :

Calculated chemistry of [ 13575-16-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.17
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.03
TPSA :	52.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.57
Log Po/w (XLOGP3) :	2.55
Log Po/w (WLOGP) :	2.52
Log Po/w (MLOGP) :	1.2
Log Po/w (SILICOS-IT) :	2.61
Consensus Log Po/w :	2.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.04
Solubility :	0.199 mg/ml ; 0.000916 mol/l
Class :	Soluble
Log S (Ali) :	-3.3
Solubility :	0.11 mg/ml ; 0.000506 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.24
Solubility :	0.0124 mg/ml ; 0.000057 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.83

Safety of [ 13575-16-1 ]

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

Application In Synthesis of [ 13575-16-1 ]

* 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 [ 13575-16-1 ]
Downstream synthetic route of [ 13575-16-1 ]

[ 13575-16-1 ] Synthesis Path-Upstream 1~11

1
[ 84978-66-5 ]
[ 13575-16-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With trichlorophosphate In toluene at 110℃; for 48 h;	Ethyl [2-phenyl-2-oxoethyl] [AMINO-2-OXOETHANOATE] (16.5 g, 71 mmol) was dissolved in 200 [ML] of anhydrous toluene in a 1 L Parr bottle. To the solution was added 21 mL (225 mmol, 3.15 eq) of POC13. The Parr bottle was sealed, and the reaction mixture heated at an oil bath temperature of [110° C] for 48 h. The solvent and [POC13] were removed under reduced pressure to give a brown oil. To the brown oil was added 300 [ML] [H2O.] The aqueous solution was extracted twice with 150 [ML] of dichloromethane. The combined organics were dried over [MGS04,] filtered and the solvent removed in vacuo. The resulting brown solid was recrystallized from 50 [ML] of EtOH to give 12.5 g of an orange solid (80percent yield). [APOS;H] NMR (300 MHz, DMSO) 8 8.10 (s, [1H),] 7.82 (d, 2 H), 7.55 [(M,] 3 H), 4.43 (q, 2H), 1.35 (t, 3H). MS (APCI+) [M/Z 218 (M + 1)]
73%	for 3 h; Heating / reflux	A solution of N-(2-Oxo-2-phenyl-ethyl)-oxalamic acid ethyl ester (approx. 15.3 mmol) in 15 mL of POC13 was heated at reflux for 3 hr. The volume was then reduced in vacuo and the residue was cautiously partitioned between CH2C12 and 5percent aqueous Na2C03. The layers were separated and the aqueous layer was extracted with CH2C12. The organic extracts were combined, dried over MgS04, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (100percent Hexane to 20percent EtOAc/Hexane gradient) to give a pale amber solid weighing 2.44 g (11.23 mmol, 73percent over two steps). IH-NMR : 300MHz, CDC13 8 7.76 (m, 2H); 7.52 (s, 1H) ; 7.45 (m, 3H); 4.5 (quart. , 2H) ; 1.46 (t, 3H).
0.48 g	at 105℃; for 2 h;	A solution of ethyl 2-oxo-2-((2-oxo-2-phenylethyl)amino)acetate (0.58 g, 2.47 mmol) in POC13 (5 ml) was refluxed at 105°C for 2 h. The resulting reaction mixture was concentrated under reduced pressure. The obtained residue was carefully treated with saturated Na2CO3 solution (20 ml)and the mixture was extracted with DCM (2 x 15 ml). The combined organic phase was collected and washed with brine (10 ml), dried over Na2SO4, filtered and concentrated under reduced pressure yielding ethyl 5-phenyloxazole-2-carboxylate (0.48 g, 2.211 mmol). LCMS: Method C, 2.09 mm, MS: ES+ 218.18.

Reference： [1] Patent: WO2004/18428, 2004, A1, . Location in patent: Page 362
[2] Patent: WO2005/61510, 2005, A1, . Location in patent: Page/Page column 17
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 334 - 347
[4] Yakugaku Zasshi, 1956, vol. 76, p. 307[5] Chem.Abstr., 1956, p. 13874
[6] ChemMedChem, 2012, vol. 7, # 6, p. 1020 - 1030
[7] Patent: WO2017/103614, 2017, A1, . Location in patent: Page/Page column 62

2
[ 5468-37-1 ]
[ 4755-77-5 ]
[ 13575-16-1 ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: With triethylamine In dichloromethane at 0 - 20℃; for 22 h; Stage #2: for 4 h; Reflux	INTERMEDIATE 51 - PREPARATION OF Ethyl 5-phenyloxazole-2-carboxylate. ; Triethylamine (1.08 mL; 7.69 mmol) was added to a mixture of 2-amino-1-phenylethanone hydrochloride (0.550 g; 3.08 mmol) and ethyl 2-chloro-2-oxoacetate (0.369 mL; 3.23 mmol) in dichloromethane (10 ml.) at 0⁰C. The reaction mixture was then stirred at room temperature for 22 hand diluted with dichloromethane (40 ml_). The organic layer was washed successively with a saturated aqueous solution of sodium carbonate, and water. The organic layer was dried over magnesium sulfate and was concentrated under reduced pressure. The crude residue was dissolved in phosphorus (V) oxychloride (10 ml) and the solution was refluxed for 4 hours. After cooling, the volatiles were removed under reduced pressure and the residue was dissolved in dichloromethane. The organic layer was then carefully washed with a saturated aqueous solution of sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent 15 to 100percent dichloromethane in heptane) to afford 0.146 g (22percent overall yield) of ethyl 5-phenyloxazole-2-carboxylate as a solid. ESI/APCI(+) : 218 (M+H), 240 (M+Na).

Reference： [1] Patent: WO2010/142801, 2010, A1, . Location in patent: Page/Page column 161-162

3
[ 1499-53-2 ]
[ 13575-16-1 ]

Reference： [1] Patent: US9284350, 2016, B2, . Location in patent: Page/Page column 172

4
[ 2999-46-4 ]
[ 1075-06-5 ]
[ 13575-16-1 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 24, p. 3438 - 3441

5
[ 2999-46-4 ]
[ 98-86-2 ]
[ 13575-16-1 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 24, p. 3438 - 3441

6
[ 4636-16-2 ]
[ 2999-46-4 ]
[ 13575-16-1 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 24, p. 3438 - 3441

7
[ 623-33-6 ]
[ 98-86-2 ]
[ 13575-16-1 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 24, p. 3438 - 3441

8
[ 541-41-3 ]
[ 108665-44-7 ]
[ 13575-16-1 ]
[ 108665-64-1 ]

Reference： [1] Journal of Organic Chemistry, 1987, vol. 52, # 15, p. 3413 - 3420

9
[ 1006-68-4 ]
[ 13575-16-1 ]

Reference： [1] Journal of Organic Chemistry, 1987, vol. 52, # 15, p. 3413 - 3420
[2] Journal of Organic Chemistry, 1987, vol. 52, # 15, p. 3413 - 3420

10
[ 613-89-8 ]
[ 13575-16-1 ]

Reference： [1] ChemMedChem, 2012, vol. 7, # 6, p. 1020 - 1030
[2] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 334 - 347

11
[ 70-11-1 ]
[ 13575-16-1 ]

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 334 - 347

[ 13575-16-1 ] Synthesis Path-Downstream 1~54

1
[ 13575-16-1 ]
[ 1014-14-8 ]

Yield	Reaction Conditions	Operation in experiment
75%		INTERMEDIATE 52 - PREPARATION OF 5-Phenyloxazole-2-carboxylic acid.; Sodium hydroxide 2M (1 ml 2 mmol) was added to a solution of intermediate 51 (0.140 g; 0.644 mmol) in ethanol (1 ml_) and the mixture was stirred at room temperature for 2 h. The solution was acidified to pH 0-1 by addition of a solution of hydrochloric acid 6N and the resulting precipitate was collected by filtration, washed with water, and dried to furnish 0.092 g (75%) of delta-phenyloxazole^-carboxylic acid as a white solid. ESI/APCI(+): 190 (M+H). ESI/APCK-) : 188 (M-H).

Reference： [1]ChemMedChem,2012,vol. 7,p. 1020 - 1030
[2]Patent: WO2010/142801,2010,A1 .Location in patent: Page/Page column 162
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 307
Chem.Abstr.,1956,p. 13874
[4]Journal of Medicinal Chemistry,2019,vol. 62,p. 9299 - 9314

2
[ 13575-16-1 ]
[ 84978-61-0 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 307
Chem.Abstr.,1956,p. 13874

3
[ 84978-66-5 ]
[ 13575-16-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With trichlorophosphate; In toluene; at 110℃; for 48h;	Ethyl [2-phenyl-2-oxoethyl] [AMINO-2-OXOETHANOATE] (16.5 g, 71 mmol) was dissolved in 200 [ML] of anhydrous toluene in a 1 L Parr bottle. To the solution was added 21 mL (225 mmol, 3.15 eq) of POC13. The Parr bottle was sealed, and the reaction mixture heated at an oil bath temperature of [110 C] for 48 h. The solvent and [POC13] were removed under reduced pressure to give a brown oil. To the brown oil was added 300 [ML] [H2O.] The aqueous solution was extracted twice with 150 [ML] of dichloromethane. The combined organics were dried over [MGS04,] filtered and the solvent removed in vacuo. The resulting brown solid was recrystallized from 50 [ML] of EtOH to give 12.5 g of an orange solid (80% yield). ['H] NMR (300 MHz, DMSO) 8 8.10 (s, [1H),] 7.82 (d, 2 H), 7.55 [(M,] 3 H), 4.43 (q, 2H), 1.35 (t, 3H). MS (APCI+) [M/Z 218 (M + 1)]
73%	With trichlorophosphate; for 3h;Heating / reflux;	A solution of N-(2-Oxo-2-phenyl-ethyl)-oxalamic acid ethyl ester (approx. 15.3 mmol) in 15 mL of POC13 was heated at reflux for 3 hr. The volume was then reduced in vacuo and the residue was cautiously partitioned between CH2C12 and 5% aqueous Na2C03. The layers were separated and the aqueous layer was extracted with CH2C12. The organic extracts were combined, dried over MgS04, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (100% Hexane to 20% EtOAc/Hexane gradient) to give a pale amber solid weighing 2.44 g (11.23 mmol, 73% over two steps). IH-NMR : 300MHz, CDC13 8 7.76 (m, 2H); 7.52 (s, 1H) ; 7.45 (m, 3H); 4.5 (quart. , 2H) ; 1.46 (t, 3H).
0.48 g	With trichlorophosphate; at 105℃; for 2h;	A solution of ethyl 2-oxo-2-((2-oxo-2-phenylethyl)amino)acetate (0.58 g, 2.47 mmol) in POC13 (5 ml) was refluxed at 105C for 2 h. The resulting reaction mixture was concentrated under reduced pressure. The obtained residue was carefully treated with saturated Na2CO3 solution (20 ml)and the mixture was extracted with DCM (2 x 15 ml). The combined organic phase was collected and washed with brine (10 ml), dried over Na2SO4, filtered and concentrated under reduced pressure yielding ethyl 5-phenyloxazole-2-carboxylate (0.48 g, 2.211 mmol). LCMS: Method C, 2.09 mm, MS: ES+ 218.18.

Reference： [1]Patent: WO2004/18428,2004,A1 .Location in patent: Page 362
[2]Patent: WO2005/61510,2005,A1 .Location in patent: Page/Page column 17
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 9299 - 9314
[4]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347
[5]Bioorganic and Medicinal Chemistry,2019,vol. 27
[6]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 307
Chem.Abstr.,1956,p. 13874
[7]ChemMedChem,2012,vol. 7,p. 1020 - 1030
[8]Patent: WO2017/103614,2017,A1 .Location in patent: Page/Page column 62

4
[ 13575-16-1 ]
[ 90770-99-3 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

5
[ 13575-16-1 ]
[ 74-89-5 ]
[ 90831-39-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1032 - 1039

6
[ 541-41-3 ]
[ 108665-44-7 ]
[ 13575-16-1 ]
[ 108665-64-1 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3413 - 3420

7
[ 1006-68-4 ]
[ 13575-16-1 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3413 - 3420
[2]Journal of Organic Chemistry,1987,vol. 52,p. 3413 - 3420

8
[ 13575-16-1 ]
[ 70594-46-6 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

9
[ 13575-16-1 ]
[ 93689-70-4 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

10
[ 13575-16-1 ]
[ 70594-50-2 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

11
[ 13575-16-1 ]
[ 90868-63-6 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669
[2]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

12
[ 13575-16-1 ]
[ 94487-79-3 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

13
[ 13575-16-1 ]
[ 95195-72-5 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 3597 - 3599
Zhurnal Obshchei Khimii,1962,vol. 32,p. 3666 - 3669

14
[ 13575-16-1 ]
[ 857334-82-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With lithium hydroxide; water; In tetrahydrofuran; methanol;	A solution of LiOH. H20 (491 mg, 11.7 mmol) in 15 mL of water was added to a stirring solution of <strong>[13575-16-1]5-phenyl-oxazole-2-carboxylic acid ethyl ester</strong> (2.42 g, 11.14 mmol) in 15 mL of THF. 3 mL of MeOH was added and the mixture was stirred overnight at room temp. The reaction mixture was then concentrated in vacuo and the resulting pale yellow solid was triturated with acetone. After removal of acetone and drying under high vacuum, a quantitative yield of the title compound as an off-white solid was obtained. LC/MS (APcI): (M+H) + = 190.1.

Reference： [1]Patent: WO2005/61510,2005,A1 .Location in patent: Page/Page column 17

15
(2R)-7-aza-[2.2.1]-Amine [ No CAS ]
[ 13575-16-1 ]
[ 500605-11-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; ethanol;	EXAMPLE 25 N-[(1S,2R,4R)-7-azabicyclo[2.2.1]hept-2-yl]-5-phenyl-1,3-oxazole-2-carboxamide Hydrochloride: <strong>[13575-16-1]Ethyl 5-phenyl-1,3-oxazole-2-carboxylate</strong> (217 mg, 1.0 mmol) is combined with (2R)-7-aza-[2.2.1]-Amine (212 mg, 1.0 mmol) in absolute EtOH (5 ml) in a sealed tube. The reaction is heated to 100 C. for 10 days. Volatiles are removed in vacuo, and the crude material is chromatographed over 25 g slurry-packed silica, eluding with 30% EtOAc/hexane. The appropriate fractions are collected and concentrated to a white solid. The solid is treated with 1M HCl in MeOH (10 ml) and stirred overnight. Volatiles are removed in vacuo, and the resulting foam is triturated with Et2O (3 ml). The slurry is filtered, and the cake washed with ether and dried overnight, affording 153 mg (48%) of Example 25. HRMS (FAB) calcd for C16H17N3O2+H: 284.1399, found 284.1391 (M+H)+.

Reference： [1]Patent: US2003/69290,2003,A1

16
[ 5468-37-1 ]
[ 4755-77-5 ]
[ 13575-16-1 ]

Yield	Reaction Conditions	Operation in experiment
22%		INTERMEDIATE 51 - PREPARATION OF Ethyl 5-phenyloxazole-2-carboxylate. ; Triethylamine (1.08 mL; 7.69 mmol) was added to a mixture of 2-amino-1-phenylethanone hydrochloride (0.550 g; 3.08 mmol) and ethyl 2-chloro-2-oxoacetate (0.369 mL; 3.23 mmol) in dichloromethane (10 ml.) at 00C. The reaction mixture was then stirred at room temperature for 22 hand diluted with dichloromethane (40 ml_). The organic layer was washed successively with a saturated aqueous solution of sodium carbonate, and water. The organic layer was dried over magnesium sulfate and was concentrated under reduced pressure. The crude residue was dissolved in phosphorus (V) oxychloride (10 ml) and the solution was refluxed for 4 hours. After cooling, the volatiles were removed under reduced pressure and the residue was dissolved in dichloromethane. The organic layer was then carefully washed with a saturated aqueous solution of sodium carbonate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent 15 to 100% dichloromethane in heptane) to afford 0.146 g (22% overall yield) of ethyl 5-phenyloxazole-2-carboxylate as a solid. ESI/APCI(+) : 218 (M+H), 240 (M+Na).

Reference： [1]Patent: WO2010/142801,2010,A1 .Location in patent: Page/Page column 161-162

17
[ 13575-16-1 ]
[ 161291-35-6 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1020 - 1030

18
[ 13575-16-1 ]
C₁₅H₁₅NO₅ [ No CAS ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1020 - 1030

19
[ 13575-16-1 ]
C₁₆H₂₂N₂O₃Si [ No CAS ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1020 - 1030

20
[ 613-89-8 ]
[ 13575-16-1 ]

Reference： [1]ChemMedChem,2012,vol. 7,p. 1020 - 1030
[2]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

21
[ 70-11-1 ]
[ 13575-16-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

22
[ 13575-16-1 ]
4-[2-(morpholin-4-ylcarbonyl)-1,3-oxazol-5-yl]benzenesulfonamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

23
[ 13575-16-1 ]
4-[2-(pyrrolidin-1-ylcarbonyl)-1,3-oxazol-5-yl]benzenesulfonamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

24
[ 13575-16-1 ]
C₁₄H₁₃ClN₂O₄S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

25
[ 13575-16-1 ]
C₁₄H₁₃ClN₂O₅S [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

26
[ 123-75-1 ]
[ 13575-16-1 ]
(5-phenyl-1,3-oxazol-2-yl)(pyrrolidin-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	at 50℃;Inert atmosphere;	General procedure: The cyclodehydration step was carried out as described in GP3.The 1,3-oxazoles 5p-t were promptly added to pyrrolidine ormorpholine (100 mmol). The reaction mixture was heated at 50 Cunder stirring for 2.5 h and cooled to room temperature. Water(150 mL) was added. The precipitate formed was filtered off,washed with water, air-dried and further crystallized from isopropylalcohol to give desired analytically pure 1,3-oxazoles 6.4.1.19 (5-phenyl-1,3-oxazol-2-yl) (pyrrolidin-1-yl)methanone (6a) Brown solid, m.p. 127-130?, yield 85% (amidation step); 1H NMR (400 MHz, DMSO-d6) delta ppm 7.80 (s, 1H, Hoxazole), 7.79 (d, J = 7.2 Hz, 2H, 2,6-HAr), 7.49 (t, J = 7.2 Hz, 2H, 3,5-HAr), 7.41 (t, J = 7.2 Hz, 1H, 4-HAr), 3.96 (t, J = 6.7 Hz, 2H, Hpyrrolidine), 3.55 (t, J = 6.7 Hz, 2H, Hpyrrolidine), 1.94 (t, J = 6.7 Hz, 4H, Hpyrrolidine); MS m/z (relative intensity) 242 (M+, 28), 116 (31), 105 (14), 102 (30), 98 (17), 89 (19), 77 (28), 70 (100), 56 (33), 55 (40), 42 (33), 41 (38), 39 (25), 29 (11); anal. calcd for C14H14N2O2 (242.28): C, 69.40; H, 5.82; N, 11.56; found: C, 69.36; H, 5.76; N, 11.49.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

27
[ 110-91-8 ]
[ 13575-16-1 ]
morpholin-4-yl(5-phenyl-1,3-oxazol-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	at 50℃;Inert atmosphere;	General procedure: The cyclodehydration step was carried out as described in GP3.The 1,3-oxazoles 5p-t were promptly added to pyrrolidine ormorpholine (100 mmol). The reaction mixture was heated at 50 Cunder stirring for 2.5 h and cooled to room temperature. Water(150 mL) was added. The precipitate formed was filtered off,washed with water, air-dried and further crystallized from isopropylalcohol to give desired analytically pure 1,3-oxazoles 4.1.20 Morpholin-4-yl(5-phenyl-1,3-oxazol-2-yl)methanone (6b) Brown solid, m.p. 93-96?, yield 79% (amidation step); 1H NMR (400 MHz, DMSO-d6) delta ppm 7.81 (s, 1H, Hoxazole), 7.79 (d, J = 7.2 Hz, 2H, 2,6-HAr), 7.50 (t, J = 7.2 Hz, 2H, 3,5-HA), 7.42 (t, J = 7.2 Hz, 1H, 4-HAr), 4.12 (m, 2H, Hmorpholine), 3.69 (m, 6H, Hmorpholine); MS m/z (relative intensity) 258 (M+, 18), 172 (31), 171 (25), 116 (57), 114 (12), 105 (19), 102 (30), 89 (23), 86 (100), 77 (35), 70 (30), 63 (12), 56 (57), 42 (42), 41 (12), 39 (13), 30 (16), 29 (38); anal. calcd for C14H14N2O3 (258.28): C, 65.11; H, 5.46; N, 10.85; found: C, 65.01; H, 5.46; N, 10.87.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 334 - 347

28
[ 1499-53-2 ]
[ 13575-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In toluene;Reflux;	To a solution of intermediate 92-b (1.10 g, 4.68 mmol) in toluene (5.0 mL) was added phosphorus oxychloride (2.18 mL, 23.38 mmol). The reaction mixture was heated at reflux overnight and cooled to room temperature. Ethyl acetate and saturated aqueous NaHCO3 were added; the organic layer was separated, washed with saturated aqueous NaHCO3, water and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 92-c as a white solid. MS m/z M+1=218.1

Reference： [1]Patent: US9284350,2016,B2 .Location in patent: Page/Page column 172

29
[ 13575-16-1 ]
C₃₃H₄₂FN₅O₄*2ClH [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

30
[ 13575-16-1 ]
C₁₀H₆NO₃^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; at 0 - 20℃; for 3h;	To a solution of intermediate 92-c (200 mg, 0.921 mmol) in THF was added 1 N aqueous NaOH (1.1 mL, 1.105 mmol) at 0 C. After stirring at room temperature for 3 hours, the reaction mixture was concentrated in vacuo to give 5-phenyloxazole-2-carboxylic acid, sodium salt (92-d) as a white solid. MS m/z M+1=190.2

Reference： [1]Patent: US9284350,2016,B2 .Location in patent: Page/Page column 172; 173

31
[ 13575-16-1 ]
C₃₈H₅₀FN₅O₆ [ No CAS ]

Reference： [1]Patent: US9284350,2016,B2

32
[ 2999-46-4 ]
[ 98-86-2 ]
[ 13575-16-1 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3438 - 3441

33
[ 623-33-6 ]
[ 98-86-2 ]
[ 13575-16-1 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3438 - 3441

34
[ 4636-16-2 ]
[ 2999-46-4 ]
[ 13575-16-1 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3438 - 3441

35
[ 2999-46-4 ]
[ 1075-06-5 ]
[ 13575-16-1 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3438 - 3441

36
[ 13575-16-1 ]
[ 270912-72-6 ]
tert-butyl 3-((5-phenyloxazole-2-carboxamido)methyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.25 g		To a solution of <strong>[13575-16-1]ethyl 5-phenyloxazole-2-carboxylate</strong> (0.46 g, 2.12 mmol) in THF (5 ml) wasadded DIPEA (0.82 g, 6.35 mmol) at 0C and stirred for 15 mi Tert-butyl 3-(aminomethyl)pyrrolidine- 1 -carboxylate (0.53 g, 2.64 mmol) was added to the reaction mixture at 0C followed by slow addition of TMA (2 M in toluene; 5.29 ml, 10.6 mmol) at 0C. The resulting reaction mixture was heated at 70C for 5 hr. The resulting reaction mixture was quickly poured into ice cold water (25 ml) and filtered through celite hyflow. The filtrate was extracted with EtOAc (3 x15 ml). The combined organic phase was collected and washed with brine (10 ml), dried over Na2SO4, filtered and concentrated under reduced pressure yielding tert-butyl 3 -((5 -phenyloxazole-2- carboxamido)methyl)-pyrrolidine-1-carboxylate (0.25 g, 0.673 mmol). LCMS: Method C, 2.28 mm, MS: ES+ 372.4.

Reference： [1]Patent: WO2017/103614,2017,A1 .Location in patent: Page/Page column 62

37
[ 2999-46-4 ]
[ 98-88-4 ]
[ 13575-16-1 ]

Reference： [1]ChemCatChem,2019,vol. 11,p. 4272 - 4275

38
[ 2999-46-4 ]
[ 98-88-4 ]
[ 13575-16-1 ]
[ 32998-97-3 ]