6317-37-9|5-Nitrothiophene-2-carboxylic acid| Ambeed

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Quality Control of [ 6317-37-9 ] Purity: 95% SDS Specification

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Product Details of [ 6317-37-9 ]

CAS No. :	6317-37-9
Formula :	C₅H₃NO₄S
M.W :	173.15
SMILES Code :	C1=C(SC(=C1)[N+](=O)[O-])C(O)=O
MDL No. :	MFCD00159552
Boiling Point :	No data available
InChI Key :	UNEPVPOHGXLUIR-UHFFFAOYSA-N
Pubchem ID :	80591

Safety of [ 6317-37-9 ]

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

Computational Chemistry of [ 6317-37-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	40.1
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	111.36 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.44
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	1.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.35
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.	-0.57
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	-0.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.54

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.14
Solubility	1.26 mg/ml ; 0.00727 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.	-3.57
Solubility	0.0465 mg/ml ; 0.000269 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	-0.42
Solubility	66.3 mg/ml ; 0.383 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	No
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	No
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.	-6.21 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.	0.56

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	2.0 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)	2.41

Application In Synthesis of [ 6317-37-9 ]

* 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 [ 6317-37-9 ]
Downstream synthetic route of [ 6317-37-9 ]

[ 6317-37-9 ] Synthesis Path-Upstream 1~1

1
[ 6317-37-9 ]
[ 112887-68-0 ]

References: [1] Patent: CN107616976, 2018, A, .
[2] Patent: CN107616976, 2018, A, .

[ 6317-37-9 ] Synthesis Path-Downstream 1~21

1
[ 1117-96-0 ]
[ 6317-37-9 ]
[ 5751-84-8 ]

References: [1]Chemische Berichte,1943,vol. 76,p. 419,428.

2
[ 16689-02-4 ]
[ 6317-37-9 ]

References: [1]Chemische Berichte,1943,vol. 76,p. 419,428.

3
[ 39565-00-9 ]
[ 6317-37-9 ]
(5-nitro-[2]thienyl)-glyoxylic acid [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1952,p. 701.

4
[ 67-56-1 ]
[ 6317-37-9 ]
[ 5832-01-9 ]

References: [1]Helvetica Chimica Acta,2002,vol. 85,p. 4485 - 4517.
[2]Journal of the American Chemical Society,1952,vol. 74,p. 1356.
[3]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1379 - 1382.
[4]European Journal of Medicinal Chemistry,2018,vol. 158,p. 302 - 310.

5
[ 6317-37-9 ]
[ 108-24-7 ]
5-acetylimino-4,5-dihydro-thiophene-2-carboxylic acid [ No CAS ]

References: [1]Doklady Akademii Nauk SSSR,1959,vol. 126,p. 86.
Doklady Chemistry, 124-129 <1959> 331,.

6
[ 6317-37-9 ]
[ 39978-57-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride;Reflux;	In a 50 ml three-necked flask, 10 g of <strong>[6317-37-9]5-nitro-2-thiophenecarboxylic acid</strong> and 29.1 ml of oxalyl chloride were added and the mixture was heated to reflux for 3 to 4 hours.The reaction was monitored by TLC to the end point (n-hexane:ethyl acetate=1:1).The reaction solution was transferred to a 100-ml single-necked flask and concentrated under reduced pressure until no more drops were directly used in the next step without purification. The yield was calculated as 100percent.
100%	With thionyl chloride;Reflux;	In a 50 ml three-neck flask, 10 g of <strong>[6317-37-9]5-nitro-2-thiophenecarboxylic acid</strong> and 29.1 ml of thionyl chloride were added and the reaction was heated to reflux for 3 to 4 hours. The reaction was monitored by TLC to the end point (n-hexane:ethyl acetate = 1:1). . The reaction solution was transferred to a 100-ml single-mouth flask and concentrated under reduced pressure until no liquid droplets was removed. It was used in the next step without purification, and the yield was calculated as 100percent.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;	Example 208 Preparation of cvclooctyl 5-r((r(1 S)-1-r(4-hvdroxyphenyl)methvn-2-(((3S)-1- r(3-hvdrochiyphenv0methvpi-3-piper8dinyl}amino)-2-oxoethvnamino)carbonvhamino1-2-thiophenecarboxylate 5-Nitro-2-thiophenecarboxylic acid (1.0 g, 5.7 mmol) was suspended in methylene chloride (10 ml_). Oxalyl chloride in methylene chloride (2.0 M, 6.0 ml_) EPO <DP n="39"/>was added at room temperature followed by one drop of dimethyl formamide (0.1 ml_). The reaction mixture was stirred at RT for 1 hr and concentrated. Methylene chloride (20 ml_) was added, concentrated again and redissolved in methylene chloride (10 ml_). N, N'-Dimethylaminopyridine ( 236 mg, 1.44 mmol) , triethyl amine( 1.61 ml_, 11.56mmol) and cyclooctanol (1.11 g, 8.67 mmol) were added to reaction mixture and stirred at room temperature overnight. The reaction mixture was filtered through a pad of silica gel (100g), eluting with methylene chloride. Cyclooctanol 5-nitro-2-thiophenecarboxylate was obtained after concentration. To cyclooctanol 5-nitro-2-thiophenecarboxylate in ethyl alcohol (20 ml_) was added palladium on carbon (10percent, 2 g). The reaction mixture was hydrogenated at 15 psi overnight. Cyclooctanol 5-amino-2-thiophenecarboxylate (1.3 g, 89.7percent) was obtained after filtration and concentration. LCMS (ESI) 254.2 [M+H]+.

	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;	Example 247; Preparation of /V-f(3S)-1-r(3-hvdroxylphenyl)methvn-1-methyl-3- piperidiniumyl)-Lambda<f-r((5-r(cvclohexyloxy)carbonvpi-2-thienyl)amino)carbonvn- L-tyrosinamide trifluoroacetate; 5-Nitro-2-thiophenecarboxylic acid (2.8 g, 16 mmol) was suspended in methylene chloride (50 ml_). Oxalyl chloride in methylene chloride (2.0 M, 32.3 ml_) was added at room temperature followed by one drop of dimethyl formamide (0.1 mL). The reaction mixture was stirred at RT for 1 hr and concentrated. Methylene chloride (100 mL) was added, concentrated again and redissolved in methylene chloride (60 mL). N, N'-Dimethylaminopyridine (652 mg, 5.33 mmol) , triethyl amine(4.47 mL, 32 mmol) and cyclohexanol (2.54 mL, 24 mmol) were added to reaction mixture and stirred at room temperature overnight. The reaction mixture was filtered through a pad of silica gel (250 g), eluting with methylene chloride. Cyclohexyl 5-nitro-2-thiophenecarboxylate was obtained after concentration. LCMS (ESI) 256 [M+H]+.
	With thionyl chloride; for 0.5h;Cooling with ice; Reflux; Inert atmosphere;	General procedure: General method: According to the method described in literature,8,9 <strong>[6317-37-9]5-nitrothiophene-2-carboxylic acid</strong> (1.0 g, 5.8 mmol) was carefully added to 6 ml of SOCl2 in a ice-cooled round bottom flask. The solution was refluxed and stirred under N2 for 30 min, cooled and evaporated under reduced pressure to obtain the corresponding acyl chloride as a sticky solid. The solid was dissolved into dry CH2Cl2 (10 ml), cooled in ice-bath and the suitable amine (5.8 mmol) was slowly added followed by TEA (0.89 ml, 6.44 mmol). The resulting mixture was stirred under N2 atmosphere at rt for 15 min, then CH2Cl2 was evaporated under reduced pressure and the residue partitioned between AcOEt and 2 N NaOH. The organic layer was washed in succession with water, 0.5 N HCl, brine, and then dried over anhydrous Na2SO4. The solvent was evaporated to dryness and the resulted solid residue was washed with the indicated solvent and used directly in the next step.
		5-Nitrothiophene-2-carboxylic acid (2.0g) was taken in a 100mL single neck RB flask equipped with N2-inlet, to this was added CH2Cl2 (30mL), OxallylChloride (6.0mL, 3V) at 0°C and stirred for few minutes. Then DMF (few drops) was added slowly (drop wise) at same temperature until evolution of bubbles in the reaction mixture was stopped, and allowed to stir at room temperature for 3h. The reaction mixture was concentrated re-dissolved in dry CH2Cl2 and used in next step.
	With thionyl chloride; In benzene; at 0℃; for 0.5h;	General procedure: To the solution of heterocyclic acid (1 mmol) in benzene at 0°C was added SOCl2 (1.5 mmol) and reaction mixture was stirred for 30 min. Solvent was evaporated and heterocyclic acid chlorides obtained were used for next step without any purification.
	With thionyl chloride; for 3h;Reflux;	10 g of <strong>[6317-37-9]5-nitro-2-thiophenecarboxylic acid</strong> and 20 ml of thionyl chloride were added to the reaction flask. The mixture was refluxed for 3 hours, and the reaction mixture was transferred to a one-neck flask, concentrated to a liquid-free flow, and dissolved in 30 ml of dichloromethane. 13.8 g of diethyl L-glutamate, 20.6 g of triethylamine, 50 ml of dichloromethane were added to a 150 ml three-necked flask, and the mixture was stirred and cooled to 0 to 5 ° C. The concentrated dichloromethane solution of the concentrate was slowly added dropwise. After the completion of the dropwise addition, the reaction was kept for 1 hour. After completion of the reaction, it was washed successively with 100 ml of 2 mol/L hydrochloric acid and 100 ml of a saturated sodium hydrogencarbonate solution. Separating the organic phase, The residue was dried over anhydrous sodium sulfate, and then concentrated to yield 16.53 g of ethyl 2-(5-nitro-2-thiopheneyl)-L-glutamic acid, yield 79.9percent.
	With oxalyl dichloride; In tetrahydrofuran; dichloromethane; at 20℃; for 4h;	REFERENCE EXAMPLE 15; 2-Amino-5-methySarninocarbonylthiophene; a) 5-Nitrothiophepie-2-carbonyl chloride; 2.89 mL (5.78 mmol) of 2.0 M oxaiyl chloride solution in CH2CI2 were added to a solution of 2-nitro-5-thiophene carboxylic acid (500 mg, 2.89 mmol) in THF (29 mL). The reaction mixture was stirred at room temperature for 4 h. The solvent was then evaporated to dryness, and the desired compound was obtained and used in next step without further purification.
	With thionyl chloride; In methanol; at 75 - 80℃; for 2h;	Put 30g of <strong>[6317-37-9]5-nitro-2-thiophenecarboxylic acid</strong> into 50ml of thionyl chloride100ml three-necked bottle,Warming up,After controlling the internal temperature at 75 ° C ~ 80 ° C for 2 h,Take about 1 ml of the reaction solution.Derivatized by adding 2 ml of anhydrous methanol,Taking <strong>[6317-37-9]5-nitro-2-thiophenecarboxylic acid</strong> as a control,TLC detection (ethyl acetate: n-hexane = 1:1) to the end of the reaction.Transfer the reaction solution to a 250 ml single-mouth bottle.Concentrated to dryness,Add 30 ml of toluene to dryness under reduced pressure.Get green needle crystals.

References: [1]Patent: CN107400109,2017,A .Location in patent: Paragraph 0041-0043; 0054-0056; 0067-0069; 0080-0082.
[2]Patent: CN107616976,2018,A .Location in patent: Paragraph 0035-0037; 0065; 0066.
[3]Recueil des Travaux Chimiques des Pays-Bas,1933,vol. 52,p. 538,547.
[4]Journal of Medicinal Chemistry,1991,vol. 34,p. 2112 - 2120.
[5]Tetrahedron,2000,vol. 56,p. 5225 - 5239.
[6]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2067 - 2076.
[7]Patent: WO2007/18514,2007,A1 .Location in patent: Page/Page column 37; 38.
[8]Patent: WO2007/18508,2007,A1 .Location in patent: Page/Page column 55-56.
[9]Journal of Medicinal Chemistry,2008,vol. 51,p. 4866 - 4869.
[10]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713.
[11]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5965 - 5979.
[12]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1938 - 1947.
[13]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3247 - 3250.
[14]Scientia Pharmaceutica,2018,vol. 86.
[15]Patent: CN109280052,2019,A .Location in patent: Paragraph 0046; 0047.
[16]Patent: WO2010/34740,2010,A1 .Location in patent: Page/Page column 77-78.
[17]Patent: CN109280044,2019,A .Location in patent: Paragraph 0041-0043; 0052-0054; 0063-0064; 0074-0076.

7
[ 186581-53-3 ]
[ 6317-37-9 ]
[ 5832-01-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1980,p. 1331 - 1335.

8
[ 20898-85-5 ]
[ 6317-37-9 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5261 - 5264.

9
[ 6317-37-9 ]
HOBt-6-carboxamidomethyl polystyrene [ No CAS ]
C₁₃H₈N₅O₅PolS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 3.08333h;	EXAMPLE 3 (Procedure 3 for Preparation of Amides); 5-Nitro-thiophene-2-carboxylic acid (2-piperidin-l-yl-phenyl))-amide; To PS-HOBt resin (0.15 mmol) was added 2 mL of a solution of pyridine (0.09 mmol) in DCM and 0.6 mL of a solution of the carboxylic acid (0.23 mmol) in N, N-dimethyl formamide ("DMF"). The mixture was shaken at room temperature for 5 min before the addition of 0.4 mL of a solution of 1,3-diisopropylcarbodiimide ("DIC") (0.66 mmol) in DCM. The mixture was shaken at room temperature for 3 h and filtered. The resin was washed with DMF (3 x), THF (3 x) and DCM (3 x) and dried in vacuo. To this acyl resin was added a solution of 2- <n="34"/>piperidinoaniline (0.075 mmol; 0.5 eq) in anhydrous THF (1 niL) and the mixture was shaken at room temperature for 16 h. The reaction was then filtered and the resin washed with THF and DCM. The combined filtrate and washings were concentrated in vacuo to yield the product. MS: 332 (M+l). LC/MS: 100 percent purity. 1H NMR (CDCl3, 300 MHz): delta 7.95 (d, 2H), 7.5 (m, 2H), 7.2 (m, 2H), 2.85 (m, 4H), 1.8-1.6 (bm, 4H), 1.5 (bm, 2H).

References: [1]Patent: WO2007/123516,2007,A1 .Location in patent: Page/Page column 31-32.

10
[ 6317-37-9 ]
[ 154590-66-6 ]
C₂₁H₂₂FN₅O₆S [ No CAS ]