[ CAS No. 64987-08-2 ] {[proInfo.proName]}

Name: 64987-08-2|Ethyl 2-(2-aminothiazol-4-yl)-2-oxoacetate|97%
Brand: Ambeed
SKU: A212347
Price: 6.0 USD
Availability: InStock
Rating: 98 (26 reviews)

,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 64987-08-2

Structure of 64987-08-2 * 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 [ 64987-08-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 64987-08-2 ]

SDS Specification

Alternatived Products of [ 64987-08-2 ]

Product Details of [ 64987-08-2 ]

CAS No. :	64987-08-2	MDL No. :	MFCD00010414
Formula :	C₇H₈N₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XNVRKLCQBZTGNA-UHFFFAOYSA-N
M.W :	200.22	Pubchem ID :	4356513
Synonyms :

Calculated chemistry of [ 64987-08-2 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.29
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.29
TPSA :	111.25 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) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	0.3
Log Po/w (MLOGP) :	-0.94
Log Po/w (SILICOS-IT) :	2.39
Consensus Log Po/w :	0.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.52
Solubility :	6.08 mg/ml ; 0.0304 mol/l
Class :	Very soluble
Log S (Ali) :	-2.57
Solubility :	0.536 mg/ml ; 0.00268 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.78
Solubility :	3.32 mg/ml ; 0.0166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.6

Safety of [ 64987-08-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 64987-08-2 ]

* 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 [ 64987-08-2 ]
Downstream synthetic route of [ 64987-08-2 ]

[ 64987-08-2 ] Synthesis Path-Upstream 1~4

1
[ 64513-00-4 ]
[ 64987-08-2 ]

Reference： [1] Patent: US4279818, 1981, A,
[2] Patent: US4166115, 1979, A,
[3] Patent: US4331664, 1982, A,

2
[ 64485-82-1 ]
[ 64987-08-2 ]

Reference： [1] Patent: US5036064, 1991, A,

3
[ 68363-42-8 ]
[ 64987-08-2 ]

Reference： [1] Patent: US4278793, 1981, A,

4
[ 64513-00-4 ]
[ 64987-08-2 ]

Reference： [1] Patent: US4304770, 1981, A,

[ 64987-08-2 ] Synthesis Path-Downstream 1~88

1
[ 76-83-5 ]
[ 64987-08-2 ]
[ 68363-43-9 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	With triethylamine; In dichloromethane; at 0 - 20℃; for 3.25h;	Triethylamine (4.03 ml, 28.9 mmol, 1.2 equiv.) and triphenylmethyl chloride (7.92 g, 28.4 mmol, 1.2 equiv.) were added to a suspension of 98.0% ethyl 2-(2- aminothiazol-4-yl)glyoxylate (5.0 g, 24.5 mmol, 1.0 equiv.) in dichloromethane (100 mL) at 0 C. The reaction mixture was stirred for 15 min. and then allowed to warm to ambient temperature over 3 h before the solvent was evaporated in vacuo. Water (100 mL) was added and was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified by flash silica chromatography (80 g, 0 - 40% ethyl acetate/hexanes) to give a yellow solid (10 g, 92.3%). LCMS: [M+l]+, 442.7. NMR (300 MHz, DMSO-d6), delta 9.05 (s, 1H), 7.85 (s, 1H), 7.37 - 7.16 (m, 15 H), 4.07 - 3.99 (m, 2H), 1.18 - 1.10 (m, 3H).

Reference： [1]Patent: WO2017/180794,2017,A1 .Location in patent: Page/Page column 81
[2]Bioorganic Chemistry,2020,vol. 94
[3]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

2
[ 79-04-9 ]
[ 64987-08-2 ]
[ 73181-65-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 881 - 891

3
[ 64987-08-2 ]
[2-(2-Methoxy-acetylamino)-thiazol-4-yl]-oxo-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1069 - 1076

4
[ 64987-08-2 ]
[ 73181-66-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 881 - 891

5
[ 64987-08-2 ]
[ 134354-10-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 881 - 891

6
[ 64987-08-2 ]
[ 134330-31-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 881 - 891

7
[ 64987-08-2 ]
[ 134330-40-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 881 - 891

8
[ 64987-08-2 ]
[ 133076-31-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

9
[ 64987-08-2 ]
[ 133076-30-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

10
[ 64987-08-2 ]
[ 133076-26-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

11
[ 64987-08-2 ]
[ 133076-36-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

12
[ 64987-08-2 ]
[ 133076-35-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

13
[ 64987-08-2 ]
[ 133076-34-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

14
[ 64987-08-2 ]
[ 138456-49-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

15
[ 64987-08-2 ]
[ 133076-23-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

16
[ 64987-08-2 ]
[ 133076-32-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479

17
[ 64987-08-2 ]
[ 68363-44-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3476 - 3479
[2]Patent: WO2017/180794,2017,A1
[3]Bioorganic Chemistry,2020,vol. 94

18
C₁₈H₁₆O₂ [ No CAS ]
[ 64987-08-2 ]
C₂₅H₂₂N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.5%	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 80℃; for 12.0h;	To a solution of the title product of 1 (3 g, 11.36 mmol) in DMF (3 mL) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (3.27 g, 17.05 mmol), 1-hydroxy-7-azabenzotriazole (HOAt) (0.5 M in DMF, 34 ml, 17.05 mmol), triethyl amine (4 ml, 28.4 mmol), and <strong>[64987-08-2]ethyl 2-amino-4-thiazoleglyoxylate</strong> (2.96 g, 14.77 mmol). The reaction solution was heated at 80 C. for 12 hours. After removal of solvent, the crude product was purified by flash chromatography with 10% ethyl acetate in hexane to afford the product of 2 (1.8 g, mmol, 35.5% yield). LC/MS m/z 447.18 (+1); HPLC Rt: 3.95 min.

Reference： [1]Patent: US2005/176749,2005,A1 .Location in patent: Page/Page column 23-24

19
[ 64987-08-2 ]
[ 876756-26-2 ]

Yield	Reaction Conditions	Operation in experiment
39%		(1) Ethyl 2-aminothiazol-4-ylglyoxylate (4 g, 19.38 mmol) was taken into methanol (50 mL) and treated with p-toluenesulfonic acid (0.94 g, 0.25 mmol) at 85 C. for 1 hour. To this was added p-toluenesulfonic acid (3.1 g, 0.75 mmol) and stirring continued for 24 hours. p-Toluenesulfonic acid was added in 500 mg lots (2 more additions after 24 and 48 h) then stirred at 85 C. for 72 hours during which time NMR indicated >50% conversion to desired product. The reaction mixture was concentrated to ~10 mL and then diluted with ethyl acetate (200 mL) and washed 3 times with saturated aqueous sodium bicarbonate (~100 mL each) and saturated brine (100 mL). The aqueous layers were back extracted 3 times with ethyl acetate (100 mL each). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a yellow residue which was absorbed onto silica gel and purified by chromatography over a methanol deactivated silica gel column gradient eluted in 10% steps from 40 to 70% v/v ethyl acetate in hexanes and then with 100% ethyl acetate. The product containing fractions were pooled and concentrated in vacuo to give (2-amino-thiazol-4-yl)-dimethoxy-acetic acid methyl ester (1.73 g, 39%).

Reference： [1]Patent: US2006/41146,2006,A1 .Location in patent: Page/Page column 37

20
[ 300356-11-0 ]
[ 64987-08-2 ]
{2-[2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-oxo-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine; N-Bromosuccinimide; triphenylphosphine; In dichloromethane;	EXAMPLE 96 {2-[2-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-oxo-acetic Acid Ethyl Ester A solution of triphenylphosphine (238 mg, 0.91 mmol) in methylene chloride (10 mL) was cooled to 0 C. and then treated with N-bromosuccinimide (183 mg, 1.03 mmol). The reaction mixture was stirred at 0 C. until it was completely dissolved and became light purple in color. The reaction mixture was then treated with 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared in Example 92, 200 mg, 0.61 mmol) and stirred at 0 C. for 20 min and then warmed to 25 C. where it was stirred for 30 min. After such time, the reaction mixture was treated with <strong>[64987-08-2]2-(amino-thiazol-4-yl)-oxo-acetic acid ethyl ester</strong> (182 mg, 0.91 mmol) and pyridine (0.088 mL, 1.09 mmol), and the reaction mixture was stirred at 25 C. for 16 h. The reaction was then diluted with water (10 mL) and then extracted with methylene chloride (3*15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded {2-[2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-oxo-acetic acid ethyl ester (208 mg, 67%) as a clear colorless oil: EI-HRMS m/e calcd for C22H25ClN2O6S2 (M+) 513.0921, found 513.0919.
67%	With pyridine; N-Bromosuccinimide; triphenylphosphine; In dichloromethane;	EXAMPLE 96 {2-[2-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-oxo-acetic acid ethyl ester A solution of triphenylphosphine (238 mg, 0.91 mmol) in methylene chloride (10 mL) was cooled to 0 C. and then treated with N-bromosuccinimide (183 mg, 1.03 mmol). The reaction mixture was stirred at 0 C. until it was completely dissolved and became light purple in color. The reaction mixture was then treated with 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in Example 92, 200 mg, 0.61 mmol) and stirred at 0 C. for 20 min and then warmed to 25 C. where it was stirred for 30 min. After such time, the reaction mixture was treated with 2-(aminothiazol-4-yl)-oxo-acetic acid ethyl ester (182 mg, 0.91 mmol) and pyridine (0.088 mL, 1.09 mmol), and the reaction mixture was stirred at 25 C. for 16 h. The reaction was then diluted with water (10 mL) and then extracted with methylene chloride (3*15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded {2-[2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-thiazol-4-yl}-oxo-acetic acid ethyl ester (208 mg, 67%) as a clear colorless oil: EI-HRMS m/e calcd for C22H25ClN2O6S2 (M+) 513.0921, found 513.0919.

Reference： [1]Patent: US2001/39344,2001,A1
[2]Patent: US6610846,2003,B1

21
[ 463-04-7 ]
[ 64987-08-2 ]
[ 73151-11-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	a Ethyl 2-oxo-2-(4-thiazolyl)acetate A solution of amyl nitrite (5.4 ml) in tetrahydrofuran (45 ml) was added dropwise to a stirred solution of <strong>[64987-08-2]ethyl 2-amino-4-thiazoleglyoxylate</strong> (4.00 g) (Aldrich) in tetrahydrofuran (25 ml) at 60 C. When the addition was complete (1 h) the mixture was stirred at 60 C. for a further 2 h. The solvent was evaporated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The product (2.54 g) was isolated by column chromatography of the residue using gradient elution (Kieselgel: 2:1 to 1:1 hexane:ethyl acetate). numax (CHCl3)/cm-1 1737 and 1696. delta (250 MHz, CDCl3), 1.42 (3H, t, J 7.11), 4.46 (2H, q, J 7.22), 8.84 (1H, J 1.95), 8.91 (1H, d, J 1.98).

Reference： [1]Patent: US6048852,2000,A

22
[ 64987-08-2 ]
[ 18908-07-1 ]
[ 126533-25-3 ]
[ 126533-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	PREPARATION 3 Ethyl 2-(3-m-methoxyphenylureido)thiazol-4-ylglyoxylate Following a procedure similar to that described in Preparation 1, the desired compound was prepared from 5 g of ethyl 2-aminothiazol-4-ylglyoxylate, 4.5 g of m-methoxyphenyl isocyanate and 40 ml of dimethylformamide, as yellow crystals having the following physical properties. Melting Point: 182 to 185 C.