5751-81-5|Ethyl 5-methylthiophene-2-carboxylate| Ambeed

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Quality Control of [ 5751-81-5 ] Purity: 98% SDS Specification

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Product Details of [ 5751-81-5 ]

CAS No. :	5751-81-5
Formula :	C₈H₁₀O₂S
M.W :	170.23
SMILES Code :	O=C(C1=CC=C(C)S1)OCC
MDL No. :	MFCD06204329
InChI Key :	NYXZOVWQCSRKMZ-UHFFFAOYSA-N
Pubchem ID :	11019293

Safety of [ 5751-81-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 5751-81-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.38
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	45.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.45
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	2.56
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.23
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.	1.59
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	3.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.65
Solubility	0.384 mg/ml ; 0.00226 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.	-3.35
Solubility	0.0755 mg/ml ; 0.000444 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	-2.53
Solubility	0.504 mg/ml ; 0.00296 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.	-5.52 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)	2.42

Application In Synthesis of [ 5751-81-5 ]

* 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 [ 5751-81-5 ]

[ 5751-81-5 ] Synthesis Path-Downstream 1~35

1
[ 5751-81-5 ]
[ 141-78-6 ]
[ 224319-23-7 ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

2
[ 5751-81-5 ]
[ 105-37-3 ]
2-methyl-3-(5-methyl-[2]thienyl)-3-oxo-propionic acid ethyl ester [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

3
[ 2786-07-4 ]
[ 5751-81-5 ]
[ 133373-92-9 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3224 - 3229.

5
[ 5751-81-5 ]
[ 133373-99-6 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 3224 - 3229.

6
[ 5751-81-5 ]
[ 13834-64-5 ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

7
[ 5751-81-5 ]
[ 859309-58-3 ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

8
[ 5751-81-5 ]
4-methyl-5-(5-methyl-[2]thienyl)-[1,2]dithiol-3-one oxime [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

9
[ 5751-81-5 ]
[ 856359-51-8 ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

10
[ 5751-81-5 ]
2-ethyl-3-(5-methyl-[2]thienyl)-3-oxo-propionic acid ethyl ester [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

11
[ 5751-81-5 ]
3-methylsulfanyl-5-(5-methyl-[2]thienyl)-[1,2]dithiolylium; iodide [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

12
[ 5751-81-5 ]
4-methyl-3-methylsulfanyl-5-(5-methyl-[2]thienyl)-[1,2]dithiolylium; iodide [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

13
[ 5751-81-5 ]
4-ethyl-3-methylsulfanyl-5-(5-methyl-[2]thienyl)-[1,2]dithiolylium; iodide [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1955,p. 442.

14
[ 5751-81-5 ]
[ 533939-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	Zinc chloride; In chloromethyl methyl ether;	Part 2 4-chloromethyl-<strong>[5751-81-5]5-methyl-thiophene-2-carboxylic acid ethyl ester</strong> A solution of <strong>[5751-81-5]5-methyl-thiophene-2-carboxylic acid ethyl ester</strong> (20.3 g, 0.119 mol) in chloromethyl methyl ether (265 mL, 3.3 mol) is treated with zinc chloride (16.3 g, 119 mmol) and stirred overnight at room temperature. The mixture is poured into water (800 mL) and extracted with dichloromethane (3*). The combined extracts are dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue is distilled to give a mixture of desired product 4-chloromethyl-5-methyl-thiopene-2-carboxylic acid ethyl ester and 3,4-bis-chloromethyl-<strong>[5751-81-5]5-methyl-thiophene-2-carboxylic acid ethyl ester</strong> (3:1, 25.9 g) as a colorless oil which is used without further purification: bp 145-175 C./ 9 mbar.

References: [1]Patent: US2003/166668,2003,A1 .

15
[ 1918-79-2 ]
[ 5751-81-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sulfuric acid; In ethanol;	Part 1 5-methyl-thiophene-2-carboxylic acid ethyl ester A solution of 5-methyl-thiophene-2-carboxylic acid (25.2 g, 177 mmol) in EtOH (500 mL) is treated with conc. H2SO4 (15 mL) and heated to a gentle reflux for 72 h. The solution is partially concentrated and poured into water (500 mL) and extracted with Et2O (3*). The combined extracts are washed with aq Na2CO3, water, dried over Na2SO4, filtered and concentrated in vacuo. Vacuum distillation of the residue afforded 5-methyl-thiophene-2-carboxylic acid ethyl ester (25.6 g, 85percent): bp 98-99° C./9-10 mbar; 1H NMR (CDCl3, 300 MHz) delta7.6 (s, 1 H), 6.78 (s, 1 H), 4.30 (q, J=6.0 Hz, 2 H), 2.50 (s, 3 H), 1.34 (t, J=6.0 Hz, 3 H).

References: [1]Patent: US2003/166668,2003,A1 .

Yield	Reaction Conditions	Operation in experiment
		Ethyl 5-methyl-2-thiophenecarboxylate To a stirred solution of 15.9 g (77.4 mmol) of 1,3-dicyclohexylcarbodiimide in 40 mL dichloromethane was added 10 g (70.3 mmol) of 5-methyl-2-thiophenecaboxylic acid and 4.85 g (105.5 mmol) of anhydrous ethanol. 0.86 g of dimethylaminopyridine was then added and the suspension stirred at room temperature for 20 hours. The resulting white precipitate was removed by filtration. The filtrate was washed with water, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by bulb-to-bulb distillation (bp=95° C. 3 mm Hg) to give the title compound as a clear, pale yellow oil. PMR (CDCl3): delta1.36 (3H, t, J=7.1 Hz), 2.52 (3H, s), 4.32 (2H, q, J =7.1 Hz), 6.76 (1H, d, J =3.8 Hz), 7.61 (1H, d, J =3.8 Hz).

17
[ 128-08-5 ]
[ 5751-81-5 ]
ethyl 5-(bromomethyl)thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dibenzoyl peroxide;SiO2; In water; ethyl acetate; benzene;	Ethyl 5-bromomethyl-2-thiophenecarboxylate N-Bromosuccinimide (23.5 g, 132 mmol), benzoyl peroxide (0.26 g) and 90 mL of benzene were brought to reflux under argon. Ethyl 5-methyl-2-thiophenecarboxylate (22.5 g, 132 mmol) was added dropwise through an addition funnel and the resulting mixture was refluxed for 6 hours and then cooled to room temperature and stirred for 16 hours. The mixture was treated with 50 mL of water and extracted with 3*75 mL ether. The ether extracts were combined and washed with 75 mL saturated aqueous NaCl and then dried (MgSO4). The solvent was removed in-vacuo and the residual oil purified by flash chromatography (SiO2, 99:1, ethyl acetate in hexanes) to give the title compound as a clear, yellow oil. PMR (CDCl3): delta1.37 (3H, t, J=7.3 Hz), 4.35 (2H, q, J=7.3 Hz), 4.68 (3H, s), 7.09 (1H, d, J =4.0 Hz), 7.64 (1H, d, J =4.0 Hz).
	With dibenzoyl peroxide; In water; benzene;	Ethyl 5-bromomethyl-2-thiophenecarboxylate (Compound 21) N-Bromosuccinimide (23.5 g, 132 mmol), benzoyl peroxide (0.26 g) and 90 mL of benzene were brought to reflux under argon. Ethyl 5-methyl-2-thiophenecarboxylate (Compound 20, 22.5 g, 132 mmol) was added dropwise through an addition funnel and the resulting mixture was refluxed for 6 hours and then cooled to room temperature and stirred for 16 hours. The mixture was treated with 50 mL of water and extracted with 3*75 mL ether. The ether extracts were combined and washed with 75 mL saturated aqueous NaCl and then dried (MgSO4). The solvent was removed in-vacuo and the residual oil purified by flash chromatography (SiO2, 99:1, hexane:ethyl acetate) to give the title compound as a clear, yellow oil. PMR (CDCl3): delta1.37 (3H, t, J=7.3 Hz), 4.35 (2H, q, J=7.3 Hz), 4.68 (3H, s), 7.09 (1H, d, J=4.0 Hz), 7.64 (1H, d, J=4.0 Hz).

References: [1]Patent: US5324840,1994,A .
[2]Patent: US5391753,1995,A .

18
[ 5751-81-5 ]
sodium thiosulfate [ No CAS ]
[ 189331-49-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; In acetonitrile;	<strong>[5751-81-5]5-Methyl-2-thiophenecarboxylic acid ethyl ester</strong> (1.84 g) was dissolved in acetonitrile (30 ml), and sulfuryl chloride (1.31 ml) in acetonitrile (20 ml) was added dropwise. The mixture was stirred for 1.5 hour over a water bath, and 10percent aqueous sodium thiosulfate (100 ml) was added. The mixture was stirred at room temperature for 2 hours and extracted with diethyl ether. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the desired fractions were concentrated under reduced pressure to give 4-chloro-5-methyl-2-thiophenecarboxylic acid ethyl ester (1.67 g).

References: [1]Patent: US5840917,1998,A .

19
[ 5751-81-5 ]
[ 1185853-40-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	With chlorosulfonic acid; at -4℃; for 3h;	delta-Methyl-thiophene^-carboxylic acid ethyl ester (11.7 mmol) is dissolved in Chlorosulfonic acid (4 ml) at -4 °C and stirred 3 hours. The reaction solution is diluted with dichloromethane and ice water is added. The organic layer is washed with water, dried over MgSO4 and the solvent is removed in vacuo. 4-Chlorosulfonyl-5-methyl-thiophene-2- carboxylic acid ethyl ester is obtained as brown oil in a yield of 35 percent. HPLC (Method A): 3.57 min, LCMS (Method A): 2.48 min, 269.0 m/z(MH+)

References: [1]Patent: WO2009/106203,2009,A1 .Location in patent: Page/Page column 63.

20
[ 554-14-3 ]
[ 56-23-5 ]
[ 64-17-5 ]
[ 5751-81-5 ]

References: [1]Petroleum Chemistry,2008,vol. 48,p. 471 - 478.

21
[ 554-14-3 ]
[ 541-41-3 ]
[ 5751-81-5 ]

References: [1]Molecules,2010,vol. 15,p. 3121 - 3134.

22
[ 5751-81-5 ]
ethyl 5-(bromomethyl)thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux;	To a solution of compound SI-14 (400 mg, 2.35 mmol) in CCl4 (20 mL) was added BPO(60 mg, 0.235 mmol) and NBS (628 mg, 3.53 mmol) and the reaction mixture was stirred atreflux for 2 hours. Then, the mixture was extracted with CH2Cl2. The organic layer was washed with aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered andconcentrated to give the crude compound which was purified by preparative TLC to obtainpure Int. 5 (494 mg, 85percent) as a yellow oil. ESI-MS m/z 249 [M+H]+ calc. for C8H9BrO2S.This intermediate was used in the next step without further characterization.
1.3 g	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux;	To a solution of reagent KR-39 (i .9 g, 0.Oi i mol) in 0014 (30 mL) was addedBPO (2i2 mg, 0.O0immol) and NBS (2.85 g, 0.0i6 mmol), then the reactionmixture was stirred at reflux for 2 hrs until TLC ( PEI EtOAc = 5:i ) showedthe starting material was consumed completely, the mixture was extracted with DOM, the organic layer was washed with aqueous NaHCO3, brine, dried over anhydrous Na2504, concentrated to give the crude compound which was purified by silica gel chromatography ( PE/ EtOAc = 5:1 ) to give pure reagent R-1 1k (1 .3 g, 48.1percent) as a yellow oil. ESI-MS (Mi-i): 249.1 calc. for C8H9BrO2S: 247.9.
1.3 g	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Reflux;	Preparation of reagent R-12b: ethyl 5-(bromomethyl)thiophene-2-carboxylate To a solution of reagent KR-5 (1 .9 g, 0.01 1 mol) in CCI4 (30 mL) was added benzoyl peroxide (BPO) (212 mg, 0.001 mmol) and /V-Bromosuccinimide (NBS) (2.85 g, 0.016 mmol), then the reaction mixture was stirred at reflux for 2 h until TLC (PE/ EtOAc = 5:1 ) showed the starting material was consumed completely, the mixture was extracted with DCM, the organic layer was washed with aqueous NaHCO3, brine, dried over anhydrous Na2SO4, concentrated to give the crude compound which was purified by silica gel chromatography (PE/ EtOAc = 5:1 ) to give pure reagent R-12b (1 .3 g, 48.1 percent) as a yellow oil. ESI-MS (M+1 ): 249.1 calc. for C8H9BrO2S: 247.9.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.
[2]Molecules,2010,vol. 15,p. 3121 - 3134.
[3]Patent: WO2014/131855,2014,A1 .Location in patent: Page/Page column 72; 73.
[4]Patent: WO2016/20307,2016,A1 .Location in patent: Page/Page column 46; 47.

23
[ 5751-81-5 ]
[ 1256286-44-8 ]

References: [1]Synthesis,2010,p. 2965 - 2968.

24
[ 1918-79-2 ]
[ 75-03-6 ]
[ 5751-81-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 2h;	To a solution of commercially available 5-methylthiophene-2-carboxylic acid (SI-13) (1.0g, 7.04 mmol) and K2CO3 (1.94 g, 14.08 mmol) in DMF (10 mL), CH3CH2I (1.65 g, 10.56mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2hours. Then, the reaction was quenched with water and extracted with EtOAc. The organiclayer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated togive compound SI-14 (400 mg, 34percent) as a pale yellow oil. ESI-MS m/z 171 [M+H]+ calc.for C8H10O2S. This intermediate was used in the next step without further purification orcharacterization.
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	To a solution of commercially available 5-methylthiophene-2-carboxylic acid(9.2 g, 0.065 mol) in DMF (80 mL) was added K2003 (17.9 g, 0.13 mol), thencompound CH3CH2I (15.2 g, 0.98 mol) was added slowly. The reactionmixture was stirred at room temperature overnight. After TLC ( PE/ EtOAc =2:1 ) showed the starting material was consumed completely, the mixture was quenched with water and extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the crude reagent KR-39 (9.5 g, 86.3percent) as a pale yellow oil which was used for the next step without further purification. ESI-MS (Mi-i): 171.0 calc. forC8H1002S:170.0.
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Preparation of reagent KR-5: ethyl 5-methylthiophene-2-carboxylate To a solution of commercially available 5-methylthiophene-2-carboxylic acid (9.2 g, 0.065 mol) in DMF (80 ml_) was added K2CO3 (17.9 g, 0.13 mol), then compound CH3CH2I (15.2 g, 0.98 mol) was added slowly. The reaction mixture was stirred at room temperature overnight. After TLC (PE/ EtOAc = 2:1 ) showed the starting material was consumed completely, the mixture was quenched with water and extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the crude reagent KR-5 (9.5 g, 86.3percent) as a pale yellow oil which was used for the next step without further purification. ESI-MS (M+1 ): 171 .0 calc. for C8H10O2S:170.0.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.
[2]Patent: WO2014/131855,2014,A1 .Location in patent: Page/Page column 63; 64.
[3]Patent: WO2016/20307,2016,A1 .Location in patent: Page/Page column 45.

25
[ 35490-05-2 ]
[ 5751-81-5 ]

Yield	Reaction Conditions	Operation in experiment
63%		Formula (1) as a sign that the compound (0.10 g, 0.50 mmol) in a stirred solution (2.5 mL AcOH solvent) to Mn (OAc) 3.2 H2O (6.7 mg, 0.025 mmol) and CoCl2 (1.3 mg, 0.01 mmol) was added. The reaction mixture and air was vigorously stirred for 3 hours at 25 ° C was added Lawesson's Reagent (0.61 g, 1.5 mmol). The mixture was heated for 1 hour at 90 ° C and cooled to room temperature (room temperature). Quench the mixture with saturated NaHCO3 (saturated NaHCO3) and extracted with CH2Cl2. The organic phase (organic phase) to H2O and brine (brine) wash, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification of the crude product by silica gel flash column chromatography to give the compound (54 mg, 0.32 mmol) represented by the formula (8) of a yellow oil type (63percent yield).

References: [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2588 - 2599.
[2]Patent: KR2016/24702,2016,A .Location in patent: Paragraph 0112-0115.

26
[ 5751-81-5 ]
ethyl 5-[[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6Hpyrazolo[4,3-d]pyrimidin-5-yl)phenyl]methyl]thiophene-2-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

27
[ 5751-81-5 ]
5-[[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl]methyl]thiophene-2-carboxylic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

28
[ 5751-81-5 ]
5-[[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl]methyl]-N-tetrahydropyran-2-yloxythiophene-2-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

29
[ 5751-81-5 ]
5-[[4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl]methyl]thiophene-2-carbohydroxamic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

30
[ 5751-81-5 ]
5-[[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-2-yl)phenyl]methyl]thiophene-2-carbohydroxamic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

31
[ 5751-81-5 ]
5-[[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-2-yl)phenyl]methyl]-N-tetrahydropyran-2-yloxythiophene-2-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

32
[ 5751-81-5 ]
5-[[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-2-yl)phenyl]methyl]thiophene-2-carboxylic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

33
[ 5751-81-5 ]
ethyl 5-[[4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-2-yl)phenyl]methyl]thiophene-2-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524.

34
C₁₄H₂₂N₂O₂S⁽²⁺⁾*2BF₄^(1-) [ No CAS ]
[ 5158-46-3 ]
[ 5751-81-5 ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 10697 - 10701.
Angew. Chem.,2018,vol. 130,p. 10857 - 10861,5.

35
[ 2810-04-0 ]
[ 5751-81-5 ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 10697 - 10701.
Angew. Chem.,2018,vol. 130,p. 10857 - 10861,5.

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
[ 5751-81-5 ]

Esters

A114742 [50340-79-9]

5-(Methoxycarbonyl)thiophene-2-carboxylic acid

Similarity: 0.96

A156236 [67808-64-4]

Methyl 5-formylthiophene-2-carboxylate

Similarity: 0.96

A150394 [81452-54-2]

Methyl 3-methylthiophene-2-carboxylate

Similarity: 0.84

A139551 [59614-94-7]

Ethyl 4-chlorothiophene-2-carboxylate

Similarity: 0.83

A428602 [160744-13-8]

Methyl 5-(2-hydroxyethyl)thiophene-2-carboxylate

Similarity: 0.82

Precautionary Statements-General
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P321
P322
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P378
P380	Evacuate area.
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Storage
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P401
P402	Store in a dry place.
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Code	Phrase
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H372	Causes damage to organs through prolonged or repeated exposure
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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.: 5751-81-5

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