79836-78-5|Ethyl 2-methylthiazole-5-carboxylate| Ambeed

Structure of 79836-78-5

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Quality Control of [ 79836-78-5 ] Purity: 98% SDS Specification

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Product Details of [ 79836-78-5 ]

CAS No. :	79836-78-5
Formula :	C₇H₉NO₂S
M.W :	171.22
SMILES Code :	CCOC(=O)C1=CN=C(C)S1
MDL No. :	MFCD03840442
InChI Key :	ORCQTMZHDQSNOJ-UHFFFAOYSA-N
Pubchem ID :	12808791

Safety of [ 79836-78-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 79836-78-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.43
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	43.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.43 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.21
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.63
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.37
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.64
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.24
Solubility	0.978 mg/ml ; 0.00571 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.95
Solubility	0.192 mg/ml ; 0.00112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.16
Solubility	1.19 mg/ml ; 0.00697 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.99 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.46

Application In Synthesis of [ 79836-78-5 ]

* 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 [ 79836-78-5 ]

[ 79836-78-5 ] Synthesis Path-Downstream 1~36

1
[ 79836-78-5 ]
[ 40004-69-1 ]

Yield	Reaction Conditions	Operation in experiment
70%		b) 2-Methyl-thiazole-5-carboxylic acid To a stirred solution of <strong>[79836-78-5]2-methyl-thiazole-5-carboxylic acid ethyl ester</strong> (1.3 g, 8.0 mmol) in dioxane (12 mL) at room temperature was added NaOH (2N, 12 mL). After 1 h the reaction mixture was neutralized with HCl (IN, 12 mL), then filtered and the collected solid dried in vacuo to give the title compound (758 mg, 70percent) as an off white solid. MS: m/e = 142.0 [M-H]".
41%	With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20℃; for 16h;	To a stirred solution of compound 97 (41 g, 239.76 mmol) in THF: H2O (7: 1, 400 mL) was added lithium hydroxide monohydrate (29.49 g, 719.29 mmol) at room temperature and stirred for 16 h. The reaction was monitored by TLC. After completion of the reaction, the volatiles were removed in vacuo. The residue was diluted with water and acidified with 2 N HCl to pH~2 and extracted using EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford compound 98 (14 g, 41percent) as an off-white solid. TLC: 20percent EtOAc/ hexanes (Rf: 0.1); 1H NMR (DMSO-d6, 400 MHz): delta 13.29 (br.s, 1H), 8.16 (s, 1H), 2.69 (s, 3H); LCMS Calculated for C5H5NO2S: 143.00; Observed: 144.1 (M+1)+.
		Ethyl 2-methyl-1,3-thiazole-5-carboxylate [e.g. available from Interchim S.A.] (61 mg) in ethanol (1 ml) was treated with aqueous sodium hydroxide (2M, 0.706 ml). The clear solution was stirred at room temperature for 18 h and then treated with aqueous hydrochloric acid (2M, 0.54 ml). The solution was blown down to dryness and the residual solid dried under vacuum over phosphorus pentoxide. The solid was then suspended in dry dichloromethane (1 ml) and treated at 20° C. with oxalyl chloride (0.032 ml) and DMF (1 drop). The mixture was stirred at room temperature for 30 mins and was then added dropwise to a solution of Intermediate 16 (98 mg) in anhydrous acetonitrile (2 ml). DIPEA (0.064 ml) was added and the solution stirred at room temperature for 20 h. The mixture was diluted with dichloromethane (15 ml), washed with dilute aqueous sodium chloride (2.x.15 ml) and blown down to dryness. The residue was purified by mass directed autoprep HPLC to give a film which was further purified using an SPE cartridge (2 g, aminopropyl) which had been pre-washed with methanol. Elution with methanol gave Example 311 as a white solid (87 mg). LCMS showed MH+=429; TRET=1.94 min.

		Synthesis of (E) To a 0° C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 mL) was added aqueous sodium hydroxide solution (5 N, 50 mL) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3*100 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14 g).
		Example 311 N-[1,6-diethyI-4-(tetrahydro-2H-pyran-4-yIamino)-1H- pyrazoIo[3,4-b]pyridin-5-yl]methyl}-2-methyI-1,3-thiazole-5-carboxamideEthyl 2-methyl-1 ,3-thiazole-5-carboxylate [e.g. available from lnterchim S.A.] (61 mg) in ethanol (1ml) was treated with aqueous sodium hydroxide (2M, 0.706ml). The clear solution was stirred at room temperature for 18h and then treated with aqueous hydrochloric acid (2M, 0.54ml). The solution was blown down to dryness and the residual solid dried under vacuum over phosphorus pentoxide. The solid was then suspended in dry dichloromethane (1ml) and treated at 20°C with oxalyl chloride (0.032ml) and DMF (1 drop). The mixture was stirred at room temperature for 30mins and was then added dropwise to a solution of Intermediate 16 (98mg) in anhydrous acetonitrile (2ml). DIPEA (0.064ml) was added and the solution stirred at room temperature for 2Oh. The mixture was diluted with dichloromethane (15ml), washed with dilute aqueous sodium chloride (2 x 15ml) and blown down to dryness. The residue was purified by mass directed autoprep HPLC to give a film which was further purified using an SPE cartridge (2g, aminopropyl) which had been pre-washed with methanol. Elution with methanol gave Example 311 as a white solid (87mg). LCMS showed MH+ =
14 g	With water; sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 2.16h;	To a 0° C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 mL) was added aqueous sodium hydroxide solution (5 N, 50 mL) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3*100 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14 g).
14 g	With water; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20℃; for 2.16667h;	To a 0°C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 ml) was added aqueous sodium hydroxide solution (5 N, 50ml) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3x100 ml). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14g).
14 g	With water; sodium hydroxide; In tetrahydrofuran; at 0℃; for 2.16667h;	To a 0° C. solution of <strong>[79836-78-5]ethyl 2-methyl-thiazole-5-carboxylate</strong> (15 g, 88 mmol) in tetrahydrofuran (50 mL) was added aqueous sodium hydroxide solution (5 N, 50 mL) over 10 minutes, and the resulting solution was stirred at room temperature for another 2 hours. It was then acidified with hydrochloric acid (2 N) to pH=1 and extracted with tetrahydrofuran (3×100 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate. Most of the solvents were removed under reduced pressure and the residue was lyophilized to afford Compound (E) (14 g).

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 14639 - 14649.
[2]Patent: WO2010/127974,2010,A1 .Location in patent: Page/Page column 43; 44.
[3]Patent: WO2018/160878,2018,A1 .Location in patent: Page/Page column 279.
[4]Chemische Berichte,1940,vol. 73,p. 1240,1252.
[5]Australian Journal of Chemistry,2004,vol. 57,p. 599 - 604.
[6]Patent: US2009/131431,2009,A1 .Location in patent: Page/Page column 142.
[7]Patent: US2010/240903,2010,A1 .Location in patent: Page/Page column 14.
[8]Patent: WO2007/36733,2007,A1 .Location in patent: Page/Page column 212.
[9]Journal of Chemical Research,2011,vol. 35,p. 313 - 316.
[10]Patent: US2014/113855,2014,A1 .Location in patent: Paragraph 0279; 0288; 0289.
[11]Patent: US2018/78532,2018,A1 .Location in patent: Paragraph 0233; 0238.
[12]Patent: US2018/161279,2018,A1 .Location in patent: Paragraph 0474-0475.

2
[ 79836-78-5 ]
[ 99979-78-9 ]

References: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 1135,1138; engl. Ausg. S. 1106, 1108.

3
[ 79836-78-5 ]
[ 409316-66-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine; In ethanol; for 12h;Heating / reflux;	Preparation 9: 2-methyl-1,3-thiazole-5-carbohydrazide; EPO <DP n="44"/>The title compound was prepared in analogy to the method described in Preparation 4 starting from ethyl 2-methyl-1 ,3-thiazole-5-carboxylate (0.5g) and used without further purification. Ethanol was used instead of methanol. MS (mlz): 158.1 [MH]+.

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1953,vol. 73,p. 126.
Chem.Abstr.,1953,p. 12358.
[2]Patent: WO2006/108701,2006,A1 .Location in patent: Page/Page column 41-42.

4
[ 79836-78-5 ]
2-methyl-thiazole-5-carbonyl azide [ No CAS ]

References: [1]Helvetica Chimica Acta,1950,vol. 33,p. 306,312.

5
[ 79836-78-5 ]
[ 56012-38-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16.25h;Inert atmosphere;	To a stirred suspension of lithium aluminium hydride (3.1 g, 93.56 mmol) in dry THF (10 mL) under inert atmosphere was added compound 63 (8 g, 46.78 mmol) in dry THF (50 mL) dropwise for 15 mm at 0 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was cooled to 0 °C, quenched with15percent aqueous sodium hydroxide solution (10 mL), filtered through celite and washed withEtOAc (3 x 100 mL). The filtrate was dried over sodium sulfate, filtered and concentrated invacuo to afford compound 64 (5 g, 83percent) as an off-white solid. TLC: 50percent EtOAc/ hexanes (Rf:0.3). LC-MS: 97.32percent; 130.22 (M+1) (column; X-select CSH C18, (50 x 3.0 mm, 2.5 jim); RT0.65 mm. 2.5 mM Aq. NH4OAc: ACN: 0.8 mL/min).
78%	In chloroform;	B. 5-(Hydroxymethyl)-2-methylthiazole Using the procedure of Example 1P, but replacing ethyl thiazole-5-carboxylate with crude ethyl 2-methylthiazole-5-carboxylate provided, after silica gel chromatography using 3percent then 5percent methanol in chloroform, the desired compound, Rf 0.27, (4percent methanol in chloroform) in 78percent yield. 1 H NMR (CDCl3)delta2.32 (br, 1H), 2.70 (s, 3H), 4.80 (s, 2H), 7.46 (s, 1H). Mass spectrum: (M+H)+ =130.
		Step 1: Intermediate 15-a To a solution of ethyl 2-methylthiazole-5-carboxylate (5.82 g, 34.0 mmol) in THF (170 ml), cooled to 0 °C, was added a 1.0M solution of LiAIH4 in THF (34.0 ml, 34.0 mmol) and the reaction was slowly warmed to room temperature and stirred overnight. Water (1.3 ml) was slowly added, followed by 15percent NaOH (1.3 ml_). The solution was stirred for 2 hours at room temperature then filtered over celite. The filtrate was concentrated under reduced pressure to provide intermediate 15-a as a yellow oil.

	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;	To a solution of intermediate 7-c (22.2 g, 130.0 mmol) in THF (430 ml) cooled to 0°C was added a 1.0 M solution LiAIH4 in THF (91.0 ml, 91.0 mmol). The solution was slowly warmed to room temperature and stirred for 2 hours. Water (3.5 ml) was slowly added, followed by 3.5 ml 15percent NaOH (3.5 ml) and water (10.5 ml) and the mixture was stirred for 1 hour. The reaction was filtered through celite and the filtrate collected. Volatiles were removed in vacuo to provide intermediate 7-d as a yellow oil.
		Step 3: Intermediate 5-d; To a solution of intermediate 5-c (22.2 g, 130.0 mmol) in THF (430 ml) cooled to 0°C was added a 1.0 M solution LiAIH4 in THF (91.0 ml, 91.0 mmol) and the solution was slowly warmed to room temperature and stirred for 2 hours. Water (3.5 ml) was slowly added, followed by 3.5 ml lSpercent NaOH (3.5 ml) and water (10.5 ml) and the mixture was stirred for 1 hour. The reaction was filtered over celite and volatiles were removed under reduced pressure to provide intermediate 5-d as yellow oil.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	To a stirred solution of ethyl 2-methylthiazole-5-carboxylate (1 eq) in dry THF (5 mL) at 0
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;	Step 4: Intermediate 29-d [0172] To a solution of intermediate 29-c (22.2 g, 130.0 mmol) in THF (430 ml) cooled to 0° C. was added a 1.0 M solution of LiAlH4 in THF (91.0 ml, 91.0 mmol) and the solution was slowly warmed to room temperature and stirred for 2 hours. Water (3.5 ml) was slowly added, followed by 3.5 ml 15percent NaOH (3.5 ml) and water (10.5 ml) and the mixture was stirred for 1 hour. The reaction was filtered over celite and volatiles were removed in vacuo to provide intermediate 29-d as yellow oil.
12g	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 18h;	Step 1: Synthesis of 2-methyl-5-hydroxymethylthiazole: At room temperature, lithium aluminum hydride (8.88g, 234mmol) was dispersed in anhydrous tetrahydrofuran (THF, 100mL). The resulting mixture was cooled to 0-5°C in an ice-water bath. To the cooled mixture was dropwise added a solution of 2-methyl-5-ethoxyformylthiazole (20g,117mmol) in anhydrous tetrahydrofuran (THF, 100mL). After the completion of the dropwise addition, the reaction mixture was naturally warmed to room temperature, and was stirred for 18 hours at room temperature. To the reaction mixture was dropwise added water (10mL) at 0-5°C. After the completion of the dropwise addition, the resulting mixture was filtered. The filtrate was concentrated to produce a yellow oily substance (12g), which was directly used in the next step.

References: [1]Patent: WO2018/53157,2018,A1 .Location in patent: Page/Page column 108; 109.
[2]Patent: US5455351,1995,A .
[3]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.
[4]Journal of general chemistry of the USSR,1962,vol. 32,p. 560 - 564.
Zhurnal Obshchei Khimii,1961,vol. 32,p. 570 - 575.
[5]Patent: EP1186604,2002,A1 .Location in patent: Page 110.
[6]Patent: WO2013/177668,2013,A1 .Location in patent: Page/Page column 40-41.
[7]Patent: WO2014/5217,2014,A1 .Location in patent: Page/Page column 23; 24.
[8]Patent: WO2014/29007,2014,A1 .Location in patent: Page/Page column 22; 23.
[9]Patent: WO2014/159234,2014,A1 .Location in patent: Page/Page column 58.
[10]Patent: US2015/191473,2015,A1 .Location in patent: Paragraph 0172.
[11]Patent: EP3181554,2017,A1 .Location in patent: Paragraph 0091.

6
[ 79836-78-5 ]
[ 82190-73-6 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.

7
[ 62-55-5 ]
[ 33142-21-1 ]
[ 79836-78-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	In benzene; for 4h;Reflux; Inert atmosphere;	Example 72- [2-(5-Methyl-3-phenyl-isoxazol-4-yl)-ethyl] -thiazole-5-carboxylic acid isopropyl- amidea) 2-Methyl-thiazole-5-carboxylic acid ethyl esterTo a stirred solution of ethyl 2-chloro-2-formyl acetate (5.0 g, 33 mmol) in benzene (50 mL) at reflux under argon was added thioamide (2.5 g, 33 mmol). After 4 h the reaction mixture was cooled, diluted with water (50 mL) and neutralized to pH 7 with a saturated solution of sodium hydro gencarbonate. The reaction mixture was extracted with ethyl acetate then the combined extracts were washed with water and brine, then dried, filtered and concentrated in vacuo. Purification by chromatography (silica, 0 to 50percent ethyl acetate in heptane) gave the title compound (2.68 g, 47percent) as a yellow liquid. MS: m/e = 172.0 [M+H]+.
35%	With magnesium sulfate; In ethanol; for 24h;Inert atmosphere; Reflux;	To a stirred solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> 61 (26 g, 173.33 mmol) in ethanol (200 mL) under argon atmosphere were added ethanethioamide 62 (10 g, 133.33 mmol), dry magnesium sulfate (10 g) at RT and heated to reflux for 24 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo, diluted with EtOAc (500 mL). The combined organic extracts were washed with saturated sodium bicarbonatesolution (2 x 200 mL), brine (200 mL), dried over sodium sulfate, filtered and concentrated invacuo to obtain the crude. The crude was purified through flash column chromatography using6percent EtOAc/ hexanes to afford compound 63 (8 g, 35percent) as brown syrup. TLC: 25percent EtOAc/hexanes (Rf: 0.7); ?H-NMR (DMSO-d6, 500 MHz): oe 8.24 (s, 1H), 4.27 (q, J = 7.2 Hz, 2H),2.70 (s, 3H), 1.27 (t, J = 7.1 Hz, 3H).
33%	With magnesium sulfate; In ethanol; at 80℃; for 16h;Inert atmosphere;	To a stirring solution of compound 96 (110 g, 733.33 mmol) in ethanol (1.2 L) under Ar atmosphere were added ethanethioamide (54.99 g, 733.33 mmol) and anhydrous magnesium sulfate (55 mg, 454.66 mmol) at room temperature, followed by heating to 80 oC for 16 h. The reaction was monitored by TLC. After completion of the reaction, the volatiles were removed in vacuo. The residue was diluted with water and extracted using EtOAc. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 10percent EtOAc/hexanes to afford compound 97 (41 g, 33percent) as thick syrup. TLC: 20percent EtOAc/ hexanes (Rf: 0.3); 1H NMR (400 MHz, DMSO-d6): delta 8.26 (s, 1H), 4.29 (q, J = 7.2 Hz, 2H), 2.71 (s, 3H), 1.29 (t, J = 7.1 Hz, 3H); LCMS Calculated for C7H9NO2S: 171.04; Observed: 172.1 (M+1)+.

	In toluene; at 90℃;	Step 2: Intermediate 29-c To a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong>, 29-b (34.7 g, 230 mmol), in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol), the reaction was stirred at 90°C overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to pH 7 with a saturated aqueous solution of NaHC03. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 29-c as beige oil.
	In toluene; at 90℃;	Step 2: Intermediate 7-cTo a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong>, 7-b (34.7 g, 230 mmol) in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol). The reaction was stirred at 90°C overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to pH=7 with saturated aqueous NaHCO3. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 7-c as a beige oil.
	In toluene; at 90℃;	Step 2: Intermediate 5-c<BOLD>: </BOLD>To a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong> 5-b (34.7 g, 230 mmol) in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol). The reaction was stirred at 90°C overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to PH=7 with a saturated aqueous solution of NaHCO3. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 5-c as beige oil
	In toluene; at 90℃;	Step 2: Intermediate 29-c [0171] To a solution of <strong>[33142-21-1]ethyl 2-chloro-3-oxopropanoate</strong>, 29-b (34.7 g, 230 mmol), in toluene (250 ml) was added thioacetamide (26.0 g, 346.0 mmol), the reaction was stirred at 90° C. overnight and then cooled to room temperature, diluted with water (300 mL) and then neutralized to pH 7 with a saturated aqueous solution of NaHCO3. Ethyl acetate was added, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided intermediate 29-c as beige oil.

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.
[2]Patent: WO2010/127974,2010,A1 .Location in patent: Page/Page column 43.
[3]Patent: WO2018/53157,2018,A1 .Location in patent: Page/Page column 108; 109.
[4]Patent: WO2018/160878,2018,A1 .Location in patent: Page/Page column 278-279.
[5]Journal of Chemical Research,2011,vol. 35,p. 313 - 316.
[6]Patent: WO2013/177668,2013,A1 .Location in patent: Page/Page column 55-56.
[7]Patent: WO2014/5217,2014,A1 .Location in patent: Page/Page column 23; 24.
[8]Patent: WO2014/29007,2014,A1 .Location in patent: Page/Page column 22; 23.
[9]Chemical Communications,2014,vol. 50,p. 11358 - 11361.
[10]Patent: US2015/191473,2015,A1 .Location in patent: Paragraph 0171.

9
[ 62-55-5 ]
2-chloro-3<i>t</i>-hydroxy-acrylic acid ethyl ester [ No CAS ]
[ 79836-78-5 ]

References: [1]Chemische Berichte,1940,vol. 73,p. 1240,1252.

10
[ 62-55-5 ]
[ 4504-12-5 ]
3-Phenyl-2-[2-thioxo-prop-(Z)-ylidene]-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester [ No CAS ]
[ 79836-78-5 ]

References: [1]Australian Journal of Chemistry,2004,vol. 57,p. 599 - 604.

11
[ 79836-78-5 ]
[ 82190-77-0 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.

12
[ 79836-78-5 ]
[ 82190-74-7 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.

13
[ 79836-78-5 ]
[ 82190-78-1 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.

14
[ 79836-78-5 ]
[ 82190-75-8 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.

15
[ 79836-78-5 ]
[ 82190-76-9 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.

16
[ 79836-78-5 ]
[ 63140-11-4 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 4461 - 4465.
[2]Journal of general chemistry of the USSR,1962,vol. 32,p. 560 - 564.
Zhurnal Obshchei Khimii,1961,vol. 32,p. 570 - 575.
[3]Patent: WO2014/159234,2014,A1 .
[4]Patent: WO2018/53157,2018,A1 .

17
[ 79836-78-5 ]
[ 65735-10-6 ]

References: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 1135,1138; engl. Ausg. S. 1106, 1108.

18
[ 79836-78-5 ]
[ 117887-05-5 ]

References: [1]Zhurnal Obshchei Khimii,1959,vol. 29,p. 1135,1138; engl. Ausg. S. 1106, 1108.

19
[ 79836-78-5 ]
5-acetoxymethyl-2-(4-dimethylamino-styryl)-3-ethyl-thiazolium; perchlorate [ No CAS ]

References: [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 560 - 564.
Zhurnal Obshchei Khimii,1961,vol. 32,p. 570 - 575.

20
[ 79836-78-5 ]
[ 89775-30-4 ]

References: [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 560 - 564.
Zhurnal Obshchei Khimii,1961,vol. 32,p. 570 - 575.

21
[ 79836-78-5 ]
[ 89776-64-7 ]

References: [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 560 - 564.
Zhurnal Obshchei Khimii,1961,vol. 32,p. 570 - 575.

22
[ 70-23-5 ]
[ 62-55-5 ]
[ 79836-78-5 ]

References: [1]Patent: EP1186604,2002,A1 .Location in patent: Page 110.

23
[ 79836-78-5 ]
2-bromomethylthiazole-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	Reference Example 18 Ethyl 2-bromomethyl-5-thiazolecarboxylate A solution of ethyl 2-methyl-5-thiazole carboxylate [S. H Mashragui, P. M. Keehn, JACS 104 4461-4465 (1982)] (4.73 g, 27.68 mmol) in carbon tetrachloride (30 ml) was treated with N-bromosuccinimide (4.92 g, 27.64 mmol) and benzoyl peroxide (0.03 g). The reaction mixture was heated to reflux under a strong light for 11/4 hours. The reaction was allowed to cool to ambient temperature and filtered. The filtrate was evaporated and subjected to chromatography (CH2 Cl2) to give the title product (1.16 g, 17percent). NMR (200 MH2,DMSO-d6): delta8.4 (s, 1H), 5.06 (s, 2H), 4.33 (g, 2H), 1.3 (t, 3H).
13%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 21h;	N-bromosuccinimide (2.58 g, 14.5 mmol) and AIBN (158 mg, 0.965 mmol) were added to a stirred solution of <strong>[79836-78-5]2-methyl-5-(carboethoxy)thiazole</strong> (1.65 g, 9.65 mmol) in CCl4 (40 mL). The mixture was stirred at 80° C. for 5 h, an additional portion of AIBN (158 mg, 0.965 mmol) was added and the resulting mixture was stirred for another 16 h at 80° C. The mixture was cooled, filtered thru celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel using CH2Cl2/hexane as an eluent to give compound 13 (1.09 g, 13percent) gas a dark-red oil: MS (ES): 250 (MH+).
	With N-Bromosuccinimide; (E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile); In 2-Methylpentane; ethyl acetate;	i 2-Bromomethyl-5-thiazolecarboxylic acid, ethyl ester 2-Methyl-5-thiazolecarboxylic acid ethyl ester (3.9 g) (J. Am. Chem. Soc. 1982, 104, 4461), N-bromosuccinimide (4.1 g) and catalytic azoisobutyronitrile in ethyl acetate (150 ml) was heated at reflux and under a 500 W halogen lamp for 16 hours. The solution was washed with water, dried (MgSO4) and evaporated. Purification was by chromatography eluding with 50percent ethyl acetate in isohexane. Yield 1.5 g. MS: GC-MS: 249/251 (M+)

References: [1]Chemistry Letters,2012,vol. 41,p. 1560 - 1562.
[2]Patent: US5965741,1999,A .
[3]Patent: US6384035,2002,B1 .Location in patent: Page column 26.
[4]Patent: US6162808,2000,A .
[5]Chemical Communications,2014,vol. 50,p. 11358 - 11361.

24
[ 50496-34-9 ]
[ 62-55-5 ]
[ 79836-78-5 ]

Yield	Reaction Conditions	Operation in experiment
32%	In acetone;	Under nitrogen atmosphere, to a solution of ethyl 2-chloroformylpropionate in acetone (250 mL) was added thioacetamide (7.74 g), and the mixture was stirred at 56° C. for 6 hours, and stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=12.5/1-->10/1) to give ethyl 2-methyl-1,3-thiazole-5-carboxylate (5.74 g, 32percent). 1H NMR (CDCl3, 400 MHz) delta 8.24 (s, 1H), 4.35 (q, 2H, J=7.1 Hz), 2.75 (s, 3H), 1.37 (t, 3H, J=7.1 Hz).
32%	In acetone;	Under nitrogen atmosphere, to a solution of ethyl 2-chloroformylpropionate in acetone (250 mL) was added thioacetamide (7.74 g), and the mixture was stirred at 56°C for 6 hours, and stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate = 12.5/1 --> 10/1) to give ethyl 2-methyl-1,3-thiazole-5-carboxylate (5.74 g, 32 percent). 1H NMR (CDCl3, 400MHz) delta 8.24 (s, 1H), 4.35 (q, 2H, J=7.1Hz), 2.75 (s, 3H), 1.37 (t, 3H, J=7.1Hz).

References: [1]Patent: US2003/181496,2003,A1 .
[2]Patent: EP1479384,2004,A1 .

25
2-(N-t-butoxycarbonylamino)methyl-5-ethoxycarbonylthiazole [ No CAS ]
[ 79836-78-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; water; sodium hydrogencarbonate; Ethyl oxalyl chloride;	a) 2-(ethoxalylamino)methyl-5-ethoxycarbonylthiazole A 13 ml potion of trifluoroacetic acid was added to 4.00 g of 2-(N-t-butoxycarbonylamino)methyl-5-ethoxycarbonylthiazole under ice-cooling, and the mixture was then stirred at the same temperature for 1 hour. Then, the solvent was concentrated and evaporated under reduced pressure, and 15 ml of dichloromethane and 5 ml of an aqueous saturated sodium hydrogencarbonate solution were then added. In addition, powdery sodium hydrogencarbonate was added until a neutral state was attained. To the solution, 10 ml of dichloromethane in which 32 ml of ethyl chloroglyoxylate was dissolved was added dropwise over 10 minutes, while the reaction solution was maintained in the neutral state by adding sodium hydrogencarbonate and water. The solution was extracted with dichloromethane (10 ml*5), and the extract was washed with water (20 ml). The organic layer was dried over anhydrous magnesium sulfate, and then filtered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by a silica gel column chromatograph to obtain 3.65 g of 2-(ethoxalylamino)methyl-5-ethoxycarbonylthiazole. NMR (CDCl3) delta: 1.41 (6H, m), 4.40 (4H, m), 4.87 (2H, d, J=6.4 Hz), 7.85 (1H, br.s), 8.16 (1H, s) MS (ESI): 287 (M+ +H)

References: [1]Patent: US5990101,1999,A .

Yield	Reaction Conditions	Operation in experiment
		A. Ethyl 2-Methylthiazole-5-carboxylate Using the procedure of Example 1O but replacing thioformamide with thioacetamide provided the crude desired compound.

27
[ 79836-78-5 ]
[ 87967-95-1 ]
[ 1254970-03-0 ]

Yield	Reaction Conditions	Operation in experiment
19%	With acetic anhydride; acetic acid; at 120℃; for 144h;	Example 632- [(E)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl] -thiazole-5-carboxylic acid (tetra- hydro-pyran-4-yl)-amidea) 2-[(E)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid ethyl ester2-Methyl-thiazole-5-carboxylic acid ethyl ester (547 mg, 2.92 mmol) was dissolved in acetic anhydride (0.15 mL, 15.5 mmol) and acetic acid (0.04 mL, 2.54 mmol) then 5-methyl-3- phenyl-4-isoxazolecarbaldehyde (500 mg, 2.92 mmol) was added and the reaction mixture warmed to 1200C. After 6 days, the reaction mixture was cooled to room temperature then diluted with water and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated then purified by chromatography (silica, 0 to 30 percent ethyl acetate in heptane) to give the title compound (191 mg, 19percent) as an off-white solid after trituration with isopropylether. MS: m/e = 341.3 [M+H]+.

References: [1]Patent: WO2010/127974,2010,A1 .Location in patent: Page/Page column 80.

28
[ 79836-78-5 ]
[ 1332459-54-7 ]

References: [1]Journal of Chemical Research,2011,vol. 35,p. 313 - 316.

29
[ 79836-78-5 ]
[ 60971-72-4 ]

References: [1]Journal of Chemical Research,2011,vol. 35,p. 313 - 316.

30
[ 79836-78-5 ]
[ 1003-60-7 ]

References: [1]Patent: EP1186604,2002,A1 .

31
[ 79836-78-5 ]
C₂₆H₂₂N₂O₂S [ No CAS ]

References: [1]Chemistry Letters,2012,vol. 41,p. 1560 - 1562.

32
[ 79836-78-5 ]
MCL₀₈ [ No CAS ]

References: [1]Chemistry Letters,2012,vol. 41,p. 1560 - 1562.

33
[ 79836-78-5 ]
C₁₈H₂₂N₂O₂S [ No CAS ]
C₁₈H₂₂N₂O₂S [ No CAS ]

References: [1]Chemistry Letters,2012,vol. 41,p. 1560 - 1562.

34
[ 79836-78-5 ]
[ 173089-10-6 ]

References: [1]Chemistry Letters,2012,vol. 41,p. 1560 - 1562.

35
[ 79836-78-5 ]
C₁₇H₂₄FNO₂SSi [ No CAS ]

References: [1]Patent: WO2013/177668,2013,A1 .
[2]Patent: WO2014/5217,2014,A1 .
[3]Patent: WO2014/29007,2014,A1 .
[4]Patent: US2015/191473,2015,A1 .

36
[ 79836-78-5 ]
C₁₁H₁₀FNO₂S [ No CAS ]

References: [1]Patent: WO2013/177668,2013,A1 .
[2]Patent: WO2014/5217,2014,A1 .
[3]Patent: WO2014/29007,2014,A1 .
[4]Patent: US2015/191473,2015,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 79836-78-5 ]

Esters

A105981 [32955-22-9]

Ethyl 5-thiazolecarboxylate

Similarity: 0.89

A228005 [131748-96-4]

Ethyl 2-(trifluoromethyl)thiazole-5-carboxylate

Similarity: 0.86

A308629 [14527-44-7]

Methyl thiazole-5-carboxylate

Similarity: 0.86

A306079 [20737-48-8]

Ethyl 4-hydroxy-2-methylthiazole-5-carboxylate

Similarity: 0.83

A366896 [152300-59-9]

Ethyl 4-aminothiazole-5-carboxylate

Similarity: 0.80

Related Parent Nucleus of
[ 79836-78-5 ]

Thiazoles

A156337 [40004-69-1]

2-Methyl-5-thiazolecarboxylic acid

Similarity: 0.92

A105981 [32955-22-9]

Ethyl 5-thiazolecarboxylate

Similarity: 0.89

A228005 [131748-96-4]

Ethyl 2-(trifluoromethyl)thiazole-5-carboxylate

Similarity: 0.86

A308629 [14527-44-7]

Methyl thiazole-5-carboxylate

Similarity: 0.86

A306079 [20737-48-8]

Ethyl 4-hydroxy-2-methylthiazole-5-carboxylate

Similarity: 0.83

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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 79836-78-5

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