[ CAS No. 113853-16-0 ] {[proInfo.proName]}

Name: 113853-16-0|Ethyl 2-aminooxazole-5-carboxylate|97%
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SKU: A135089
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Quality Control of [ 113853-16-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 113853-16-0 ]

SDS Specification

Alternatived Products of [ 113853-16-0 ]

Product Details of [ 113853-16-0 ]

CAS No. :	113853-16-0	MDL No. :	MFCD06657433
Formula :	C₆H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UHUDJKCNXFBBHU-UHFFFAOYSA-N
M.W :	156.14	Pubchem ID :	5260193
Synonyms :

Calculated chemistry of [ 113853-16-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.99
TPSA :	78.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	0.44
Log Po/w (MLOGP) :	-0.58
Log Po/w (SILICOS-IT) :	0.26
Consensus Log Po/w :	0.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.29
Solubility :	8.07 mg/ml ; 0.0517 mol/l
Class :	Very soluble
Log S (Ali) :	-1.76
Solubility :	2.73 mg/ml ; 0.0175 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.35
Solubility :	7.02 mg/ml ; 0.045 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.32

Safety of [ 113853-16-0 ]

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 [ 113853-16-0 ]

* 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.

Upstream synthesis route of [ 113853-16-0 ]
Downstream synthetic route of [ 113853-16-0 ]

[ 113853-16-0 ] Synthesis Path-Upstream 1~4

1
[ 10229-12-6 ]
[ 57-13-6 ]
[ 113853-16-0 ]

Yield	Reaction Conditions	Operation in experiment
51.3%	at 100℃; for 1 h;	Ethyl 2-chloro-3-oxopropanoate (13) 4.48 g (29.8 mmol, 1.00 mol eq) and 1.79 g (29.8 mmol, 1.00 mol eq) of urea were mixed with 40 mL water. The reaction mixture was stirred at 100 °C for 1 h. A final pale yellow suspension was cooled down to RT, neutralized by a saturated aq. solution of NaHCO₃ and extracted with EA (3 x 50 mL). The combined organic layers were dried using Na₂SO₄, filtered and concentrated under reduced pressure. The crude product was purified using FLC (SiO₂, H / EA = 1 / 2) yielding 2.40 g (15.4 mmol, 51.3 percent) of ethyl 2-aminooxazole-5-carboxylate (14).

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 754 - 761

2
[ 33142-21-1 ]
[ 57-13-6 ]
[ 113853-16-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 10, p. 1379 - 1382

3
[ 33142-21-1 ]
[ 57-13-6 ]
[ 113853-16-0 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1953, vol. 286, p. 494,499

4
[ 113853-16-0 ]
[ 862599-47-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	at 60 - 80℃; for 2 h; Inert atmosphere	A mixture of 1.19 g (8.8 mmol, 1.50 mol eq) of CuCl₂ abs and 1.05 mL (8.8 mmol, 1.50 mol eq) of ^tBuONO in 30 mL of AN abs under Ar was heated to 60 °C. By this temperature 920.0 mg (5.9 mmol, 1.00 mol eq) of ethyl 2-aminooxazole-5-carboxylate (14) was added portion wise. Then the temperature was raised to 80 °C and the reaction mixture was stirred for 2 h. After the consumption of starting material 14 (TLC analysis) the reaction mixture was cooled down to RT and 15 mL of water and 8 mL of 2M HCl were added. The aqueous solution was extracted with EA (3 x 20 mL) and the combined organic layers were washed with brine, dried by Na₂SO₄, filtered and concentrated under reduced pressure yielding 850 mg (4.8 mmol, 83 percent) of ethyl 2-chlorooxazole-5-carboxylate (15) as light yellow oil. The obtained crude product 15 was sufficiently pure to be used for the further synthesis. Purification of 15 can be done by FLC (SiO₂, H / EA; 1 / 1), however because of instability of 15 on silica, the yield is lowered to approximately 40 percent.

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 754 - 761

[ 113853-16-0 ] Synthesis Path-Downstream 1~32

1
[ 33142-21-1 ]
[ 57-13-6 ]
[ 113853-16-0 ]
2-chloro-3-ureido-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1953,vol. 286,p. 494,499

2
[ 113853-16-0 ]
[ 3173-56-6 ]
[ 304696-11-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1379 - 1382

3
[ 33142-21-1 ]
[ 57-13-6 ]
[ 113853-16-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1379 - 1382

4
[ 113853-16-0 ]
[ 591-80-0 ]
ethyl 2-(pent-4-enamido)oxazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

5
[ 113853-16-0 ]
[ 13722-73-1 ]
ethyl 2-(4-methylenehexanamido)oxazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

6
[ 15781-73-4 ]
[ 113853-16-0 ]
C₁₅H₁₂N₂O₅ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 8250 - 8252

7
[ 113853-16-0 ]
ethyl 2-{N-[2-(1-methyl-1H-indol-3-yl)ethyl]pent-4-enamido}oxazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

8
[ 113853-16-0 ]
ethyl 2-{N-[2-(1-methyl-1H-indol-3-yl)ethyl]-4-methylenehexanamido}oxazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

9
[ 113853-16-0 ]
[ 869366-17-6 ]
2-[9-Chloro-7-(2,6-difluoro-phenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-oxazole-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 145℃; for 0.333333h;	A mixture of 9-Chloro-7-(2,6-difluoro-phenyl)-2-iodo-5H-benzo[c]pyrimido[4,5-e]azepine (200 mg, 0.43 mmol), <strong>[113853-16-0]ethyl 2-aminooxazole-5-carboxylate</strong> (81.2 mg, 0.52 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (935 mg, 0.034 mmol), Xantphos (30 mg, 0.052 mmol), powdered K3PO4 (183 mg, 0.86 mmol), and degassed toluene were submitted to microwave irradiation (300 W) for 20 minutes at 145 C. The mixture was cooled to room temperature and then evaporated to leave a brown solid which was purified by column chromatography (silica gel, CH2Cl2 to 50% diethyl ether in CH2Cl2) to yield 2-[9-Chloro-7-(2,6-difluoro-phenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-ylamino]-oxazole-5-carboxylic acid ethyl ester as a yellow powder (103 mg, 48%) MS m/z=496 (M+H).

Reference： [1]Patent: US2005/256102,2005,A1 .Location in patent: Page/Page column 146

10
[ 113853-16-0 ]
[ 1111881-62-9 ]
[ 1151240-87-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 - 40℃; for 384.0h;	Intermediate 8: Ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1 H-1 ,2,3-triazol-4- yl}carbonyl)amino]-1 ,3-oxazole-5-carboxylateA mixture of i-KS^-dichloropheny^methylJ-delta-methyl-I H-I ^S-triazole^-carboxylic acid (Intermediate 4) (1 g, 3.4 mmol), ethyl 2-amino-1 ,3-oxazole-5-carboxylate (0.82 g, 5.2 mmol), HOBt (0.708 g, 5.2 mmol), EDCI (1.005 g, 5.2 mmol) and NEt3 (730 mul_, 5.2 mmol) in DMF (50 ml.) was stirred at room temperature for 2 days. The reaction was not completed and 2.5 eq of EDCI and HOBt were added and the reaction was heated at 400C and stirred for a further 14 days. Again no completed reaction was obtained. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with DCM/MeOH (90/10) to give after crystallisation from diisopropyl ether, the title compound as a yellow solid (98 mg, 6%). LC/MS: m/z 424 (M+H)+. Rt: 3.17 min.

Reference： [1]Patent: WO2009/60054,2009,A1 .Location in patent: Page/Page column 36

11
[ 698-72-6 ]
[ 113853-16-0 ]
[ 1258411-48-1 ]

Yield	Reaction Conditions	Operation in experiment
20%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 70℃; for 8.0h;	Example 41[0196] To a stirred solution of <strong>[113853-16-0]ethyl 2-aminooxazole-5-carboxylate</strong> (0.10 g, 0.64 mmol) in THF (6 mL) was added DIPEA (0.12 mL, 0.70 mmol) at 0 C. After stirring for 10 min. at the same temperature, Compound 21 (0.23 mg, 1.28 mmol) was added. The mixture was stirred at 70 C for 8 h, cooled to room temperature, and diluted with EtOAc and washed with 5% NaHCO3. The organic phase was concentrated and the residue was purified by chromatography on a silica gel column eluted with 1% MeOH in CH2Cl2 to afford Compound 41 (35 mg, 20%) as a yellow solid. 1H NMR (500MHz, DMSO-J6) delta 12.43 (s, IH, NH), 7.95 (s, IH, Ar-H), 4.31 (dd, 2Eta, J= 14.3 Hz, CH2), 2.77 (dd, 2Eta, J= 14.2 Hz, CH2), 1.30 (t, 3Eta, J= 6.7 Hz, CH3), 1.23 (t, 3H, J= 7.5 Hz, CH3). MS (ESI) m/z 296 [M-H]".

Reference： [1]Patent: WO2010/144338,2010,A1 .Location in patent: Page/Page column 101

12
[ 109-09-1 ]
[ 113853-16-0 ]
[ 1380420-39-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 160℃; for 1.0h;Inert atmosphere; Microwave irradiation;	General procedure: To an oven-dried microwave vial was added <strong>[113853-16-0]ethyl 2-amino-1,3-oxazole-5-carboxylate</strong> (546 mg, 3.50 mmol), Cs2CO3 (2279 mg, 6.99 mmol), Pd2(dba)3 (80 mg, 0.09 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152 mg, 0.26 mmol) and the vial was capped and purged with nitrogen. 2,4-Dichloropyridine (0.378 mL, 3.50 mmol) was added via syringe, followed by 1,4-dioxane (18 mL) (degassed) and the reaction mixture was heated to 160 C for 1 h under microwave irradiation. CH2Cl2 (40 mL) was added to the crude reaction mixture together with silica (5 g). The solvents were removed under reduced pressure and the crude product was purified by flash silica chromatography with CH2Cl2 (containing 1% methanolic ammonia) as eluent.The resulting brown solid was triturated with Et2O to give ethyl 2-(4-chloropyridin-2-ylamino)oxazole-5-carboxylate (626 mg, 67%) as a pale yellow solid, which was collected by filtration and dried under vacuum.