[ CAS No. 14597-58-1 ] {[proInfo.proName]}

Name: 14597-58-1|Methyl 5-aminothiophene-2-carboxylate|97%
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Quality Control of [ 14597-58-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 14597-58-1 ]

Product Details of [ 14597-58-1 ]

CAS No. :	14597-58-1	MDL No. :	MFCD07687259
Formula :	C₆H₇NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NNQTUMGJWXJMIR-UHFFFAOYSA-N
M.W :	157.19	Pubchem ID :	7131725
Synonyms :

Calculated chemistry of [ 14597-58-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.0
TPSA :	80.56 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	1.44
Log Po/w (WLOGP) :	1.12
Log Po/w (MLOGP) :	0.29
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	1.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	1.72 mg/ml ; 0.011 mol/l
Class :	Very soluble
Log S (Ali) :	-2.74
Solubility :	0.288 mg/ml ; 0.00183 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.37
Solubility :	6.71 mg/ml ; 0.0427 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.15

Safety of [ 14597-58-1 ]

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 [ 14597-58-1 ]

* 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 [ 14597-58-1 ]
Downstream synthetic route of [ 14597-58-1 ]

[ 14597-58-1 ] Synthesis Path-Upstream 1~8

1
[ 5832-01-9 ]
[ 14597-58-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen In ethanol	To methyl 5-nitro-2-thiophenecarboxylate (11.55 mmol) in ethyl alcohol (20 mL) was added palladium on carbon (10percent, 1 g). The reaction mixture was hydrogenated with an atmosphere of H2 overnight. Methyl 5-amino-2-thiophenecarboxylate (1.67 g, 92percent) was obtained after filtration and concentration.LCMS (ESI) 157 [MH-H]⁺.
66%	Stage #1: With hydrogenchloride; tin(ll) chloride In ethanol; water at 20 - 35℃; for 2 h; Stage #2: basic conditions	Part A To a mixture of 2-nitrothiophene (600 mg, 3.2 mmol) and SnCl₂.2H₂O (4.86 g, 25.6 mmol) in 95percent EtOH(13.6 mL) was added concentrated HCl (13.6 mL) dropwise at room temperature (sufficient cooling was necessary to keep the reaction temperature under 35° C.). After the addition, the reaction mixture was stirred at 35° C. for 2 hours. EtOH was removed under vacuum and the aqueous layer was washed with hexane (50 mL.x.2). The pH of the aqueous layer was adjusted to pH 9 and was extracted three times with EtOAc (50 mL). The extracts were combined and dried over Na₂SO₄. After evaporation of solvent, the product was obtained as white solid (332 mg, 66percent). ¹H NMR (400 MHz, DMSO-d₆): 7.15(d, 1H), 6.60(s, 2H), 5.10(d, 1H), 3.65(s, 3H). LC-MS m/z 158.1 (M+H).

Reference： [1] Patent: WO2006/65788, 2006, A2, . Location in patent: Page/Page column 10
[2] Patent: US2007/43045, 2007, A1, . Location in patent: Page/Page column 59
[3] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 10, p. 1379 - 1382
[4] Patent: WO2004/108683, 2004, A1, . Location in patent: Page 564-565
[5] Patent: WO2004/18480, 2004, A1, . Location in patent: Page 156
[6] Patent: US2007/32475, 2007, A1, . Location in patent: Page/Page column 36-37
[7] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 708 - 713
[8] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 302 - 310
[9] Patent: WO2008/156614, 2008, A2, . Location in patent: Page/Page column 227; 228

2
[ 527-72-0 ]
[ 14597-58-1 ]
[ 89499-43-4 ]

Reference： [1] Patent: US2010/68178, 2010, A1, . Location in patent: Page/Page column 16-17

3
[ 67-56-1 ]
[ 527-72-0 ]
[ 14597-58-1 ]
[ 89499-43-4 ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: at 0 - 10℃; for 1.25 h; Stage #2: at 20℃; Reflux	Example 12: Synthesis of 4-[dimethylamino)diazenyl]thiophene-2-carboxamide (compound 12); Step a:4-Nitrothiophene-2-carboxylic acid: Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10 ⁰C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2 x 50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75percent), mp 110-118 ⁰C. The product was a mixture of two compounds by HPLC and ¹H NMR and was proceeded to the next step. Step b:Methyl 4-nitrothiophene-2-carboxylate: To a solution of nitrothiophene-2-carboxylic acids (6.8 g, 39.3 mmol) in methanol (50 mL) was added thionyl chloride (6 mL, 78.6 mmol) drop wise under stirring at rt. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with cold water and dried to give the product as an off-white solid (6.2 g, 85percent). ¹H NMR showed that, it is a mixture of two compounds and the crude product was proceded to the next step.; Step c:Methyl 4-aminothiophene-2-carboxylate: To a solution of methyl nitrothiophene-2- carboxylates (7 g, 37.43 mmol) in a mixture of water (150 mL) and methanol (50 mL) was added Cone, hydrochloric acid (4.5 mL). To the above solution was added iron powder (10.5 g, 188 mmol) followed by ammonium chloride (1O g, 187 mmol) at rt. The reaction mixture was stirred and warmed to 70 ⁰C for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with chloroform (4 x 100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10 and small amount of triethyl amine) as eluent to give methyl 4-aminothiophene-2-carboxylate (1.8 g, 31percent), mp 76-78⁰C. ¹H NMR (400 MHz, CDCl₃): δ 7.31 (IH, d, JH .6 Hz), 6.40 (IH, d, J=I.6 Hz), 3.85 (3H, s), 3.63 (2H, br s).Further elution of the column with the same solvent system provided methyl 5- aminothiophene-2-carboxylate (0.5 g, 8.5percent), mp 70-72⁰C. ¹H NMR (400 MHz, CDCl₃): δ 7.45 (IH, d, J=4.0 Hz), 6.09 (IH, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s).

Reference： [1] Patent: WO2010/29577, 2010, A2, . Location in patent: Page/Page column 38-39

4
[ 5832-01-9 ]
[ 7439-89-6 ]
[ 14597-58-1 ]

Reference： [1] Patent: US5709867, 1998, A,

5
[ 6317-37-9 ]
[ 14597-58-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 10, p. 1379 - 1382
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 708 - 713
[3] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 302 - 310

6
[ 39978-57-9 ]
[ 14597-58-1 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 9, p. 708 - 713

7
[ 527-72-0 ]
[ 14597-58-1 ]
[ 89499-43-4 ]

Reference： [1] Patent: US2010/68178, 2010, A1, . Location in patent: Page/Page column 16-17

8
[ 67-56-1 ]
[ 527-72-0 ]
[ 14597-58-1 ]
[ 89499-43-4 ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: at 0 - 10℃; for 1.25 h; Stage #2: at 20℃; Reflux	Example 12: Synthesis of 4-[dimethylamino)diazenyl]thiophene-2-carboxamide (compound 12); Step a:4-Nitrothiophene-2-carboxylic acid: Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10 ⁰C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2 x 50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75percent), mp 110-118 ⁰C. The product was a mixture of two compounds by HPLC and ¹H NMR and was proceeded to the next step. Step b:Methyl 4-nitrothiophene-2-carboxylate: To a solution of nitrothiophene-2-carboxylic acids (6.8 g, 39.3 mmol) in methanol (50 mL) was added thionyl chloride (6 mL, 78.6 mmol) drop wise under stirring at rt. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with cold water and dried to give the product as an off-white solid (6.2 g, 85percent). ¹H NMR showed that, it is a mixture of two compounds and the crude product was proceded to the next step.; Step c:Methyl 4-aminothiophene-2-carboxylate: To a solution of methyl nitrothiophene-2- carboxylates (7 g, 37.43 mmol) in a mixture of water (150 mL) and methanol (50 mL) was added Cone, hydrochloric acid (4.5 mL). To the above solution was added iron powder (10.5 g, 188 mmol) followed by ammonium chloride (1O g, 187 mmol) at rt. The reaction mixture was stirred and warmed to 70 ⁰C for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with chloroform (4 x 100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10 and small amount of triethyl amine) as eluent to give methyl 4-aminothiophene-2-carboxylate (1.8 g, 31percent), mp 76-78⁰C. ¹H NMR (400 MHz, CDCl₃): δ 7.31 (IH, d, JH .6 Hz), 6.40 (IH, d, J=I.6 Hz), 3.85 (3H, s), 3.63 (2H, br s).Further elution of the column with the same solvent system provided methyl 5- aminothiophene-2-carboxylate (0.5 g, 8.5percent), mp 70-72⁰C. ¹H NMR (400 MHz, CDCl₃): δ 7.45 (IH, d, J=4.0 Hz), 6.09 (IH, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s).

Reference： [1] Patent: WO2010/29577, 2010, A2, . Location in patent: Page/Page column 38-39

[ 14597-58-1 ] Synthesis Path-Downstream 1~88

1
[ 14597-58-1 ]
5-benzoylimino-4,5-dihydro-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1957,vol. 245,p. 80

2
[ 910472-18-3 ]
[ 14597-58-1 ]
[ 32315-10-9 ]
2-[3-(3-methoxycarbonyl-thiophen-2-yl)-ureido]-4,5,6,7,8,9-hexahydro-cycloocta[b]thiophene-3-carboxylic acid isopropyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5812 - 5832

3
[ 14597-58-1 ]
4-oxo-2-trichloromethyl-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2004,vol. 40,p. 370 - 376

4
[ 14597-58-1 ]
4-oxo-2-trifluoromethyl-3,4-dihydro-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2004,vol. 40,p. 370 - 376

5
[ 14597-58-1 ]
C₁₀H₅Cl₂F₃NO₄PS [ No CAS ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

6
[ 14597-58-1 ]
2-carbomethoxy-4-trifluoromethylthieno[2,3-b]pyridin-6-yl dimethylphosphate [ No CAS ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

7
[ 14597-58-1 ]
6-pyrrolidin-1-yl-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

8
[ 14597-58-1 ]
6-(4-methyl-piperazin-1-yl)-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

9
[ 14597-58-1 ]
6-((2R,6S)-2,6-Dimethyl-morpholin-4-yl)-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

10
[ 14597-58-1 ]
6-azepan-1-yl-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

11
[ 14597-58-1 ]
[ 633315-51-2 ]

Reference： [1]Synthesis,2003,p. 1531 - 1540

12
[ 14597-58-1 ]
[ 438495-71-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 1183 - 1184

13
[ 14597-58-1 ]
[ 897673-59-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 1183 - 1184

14
[ 14597-58-1 ]
6-methoxycarbonyl-2-methyl-1-morpholino-1-oxo-3-phenyl-1,2-dihydro-1λ⁵-thieno[3,2-e]-2,4,1-diazaphosphinine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 1183 - 1184

15
[ 14597-58-1 ]
[ 304696-17-1 ]

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

16
[ 14597-58-1 ]
3-(2-[5-(3-benzyl-ureido)-thiophene-2-carbonyl]-amino}-acetylamino)-3-pyridin-3-yl-propionic acid [ No CAS ]

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

17
[ 6317-37-9 ]
[ 14597-58-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1379 - 1382
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713
[3]European Journal of Medicinal Chemistry,2018,vol. 158,p. 302 - 310

18
[ 14597-58-1 ]
[ 24424-99-5 ]
[ 666853-39-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	In tetrahydrofuran; for 48h;Reflux;	The compound (947 mg, 5.58 mmol) obtained in Example 4a was dissolved in tetrahydrofuran (19 mL), di-tert-butyl dicarbonate (1.58 g, 7.25 mmol) was added, and then the mixture was stirred with heating to reflux for 48 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 6:1 ? 4:1, v/v) to give the title compound (971 mg; yield, 68%) as a brown solid. 1H NMR (CDCl3, 400 MHz): delta 1.53 (9H, s), 3.84 (3H, s), 6.44 (1H, d, J = 3.9 Hz), 7.21 (1H, brs), 7.56 (1H, d, J = 3.9 Hz). MS (EI) m/z: 257 (M+).
	In tetrahydrofuran; for 72h;Heating / reflux;	To a stirred solution of 96 (35 g; 187 mmol) in MeOH (400 ml) was added a suspension of 10% palladium on carbon (30 g) in [ACOH] (100 ml) The resulting suspension was exposed to 1 atmosphere of hydrogen for 8 hours after [WHICH HPLC] showed no remaining starting material. The catalyst was removed by filtration through a pad of Celite and the filtrate was evaporated to dryness and the residue purified by flash chromatography on silica gel eluting with DCM-MeOH (98: 2) to afford the amine (11.4 g) as an off-white solid, which was used immediately in the next step. To a stirred solution of the amine (11.4 g; 72.9 mmol) in THF (20 ml) was added di-tert-butyldicarbonate [( (BOC) 20)] (17.5 g; 80.2 mmol). The resulting solution was heated to reflux for 3 days after which HPLC showed no remaining starting material. The reaction mixture was evaporated to dryness and the residue obtained was triturated with diethyl ether (100 ml). The resulting precipitate was collected by filtration, washed with diethyl ether [(2X50] ml) and dried to a constant weight to afford 97 (15.1 g) as an off-white crystalline solid. Yield: 32% MS-ESI: 258 [[M+H] +] [1H] NMR [(DMSO-D6)] 1.53 (s, 9H), 3.74 (s, 3H); 6.55 (d, 1H) ; 7.57 (d, 1H).

Reference： [1]Patent: EP2409977,2012,A1 .Location in patent: Page/Page column 36
[2]Patent: WO2004/18480,2004,A1 .Location in patent: Page 156

19
[ 5832-01-9 ]
[ 7439-89-6 ]
[ 14597-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;	(a) Preparation of methyl 5-amino-2-thiophenecarboxylate 3.6 g of iron powder, 1.4 g of FeSO4.7H2 O, 25 ml of methanol and 8 ml of water were successively introduced into a three-necked flask. 940 mg (5 mmol) of methyl 5-nitro-2-thiophenecarboxylate were then added and the mixture was heated at 70 C. for eight hours. The reaction medium was filtered on celite, the filtrate evaporated, and taken up in water and ethyl ether. The organic phase was decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with dichloromethane; 2 g (77%) of the expected compound of melting point 110-112 C. were obtained.

Reference： [1]Patent: US5709867,1998,A

20
[ 14597-58-1 ]
[ 31310-08-4 ]
[ 927197-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;dmap; at 40℃;	Part B To a solution of 2-methyl-4-methoxybenzonic acid (166 mg, 1 mmol) in DCM (5 mL) at RT, oxalyl chloride (0.15 mL) was added followed by the DMF (1 drop). The resulting mixture was stirred at RT for 3 hours and the solvent was evaporated under vacuum. To the flask with the residue of acetyl chloride, DCM (15 mL) was added, followed by 2 (100 mg, 0.64 mmol), pyridine (0.2 mL) and catalytical amount DMAP. The mixture was heated up to 40 C. and was stirred at this temperature for overnight. After cooling down to room temperature, EtOAc (80 mL) was added and the organic was washed with 1 N HCl, brine and dried over Na2SO4. After evaporation of solvent, the crude product 3 was used in the next step directly. LC-MS m/z 306.1 (M+H).

Reference： [1]Patent: US2007/43045,2007,A1 .Location in patent: Page/Page column 59

21
[ 14597-58-1 ]
[ 1094070-49-1 ]
[ 1094071-35-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		Step B: To a solution of the aminoester (850 mg, 5.414 mmol)) and sulfone from Example 1 (1 equivalent, 1469 mg, 3.609 mmol) in DMSO (36 mL) was treated with NaH (60% dispersion in oil, 14.43 mmol, 577 mg) at room temperature portionwise. After 10 min, LC-MS analysis of the reaction indicated the reaction was complete. While cooling by water bath, the reaction was quenched with sat. NH4CI dropwise (5 ml) and then added H2O (160 ml) extracted with ethyl acetate (2x). The combined organic layers were washed with brine and dried (sodium sulfate). Evaporation and purification by column chromatography (0 to 100% EtOAc/Hexane) afforded title compound (1492 mg, 85%). HPLC-MS tR = 2.41 Min (UV 254nm)- Mass calculated for M+ 484.1 , observed LC/MS m/z 485.2 (M+H).

Reference： [1]Patent: WO2008/156614,2008,A2 .Location in patent: Page/Page column 227; 228
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 592 - 598

22
[ 67-56-1 ]
[ 527-72-0 ]
[ 14597-58-1 ]
[ 89499-43-4 ]

Yield	Reaction Conditions	Operation in experiment
8.5%; 31%		Example 12: Synthesis of 4-[dimethylamino)diazenyl]thiophene-2-carboxamide (compound 12); Step a:4-Nitrothiophene-2-carboxylic acid: Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10 0C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2 x 50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75%), mp 110-118 0C. The product was a mixture of two compounds by HPLC and 1H NMR and was proceeded to the next step. Step b:Methyl 4-nitrothiophene-2-carboxylate: To a solution of nitrothiophene-2-carboxylic acids (6.8 g, 39.3 mmol) in methanol (50 mL) was added thionyl chloride (6 mL, 78.6 mmol) drop wise under stirring at rt. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with cold water and dried to give the product as an off-white solid (6.2 g, 85%). 1H NMR showed that, it is a mixture of two compounds and the crude product was proceded to the next step.; Step c:Methyl 4-aminothiophene-2-carboxylate: To a solution of methyl nitrothiophene-2- carboxylates (7 g, 37.43 mmol) in a mixture of water (150 mL) and methanol (50 mL) was added Cone, hydrochloric acid (4.5 mL). To the above solution was added iron powder (10.5 g, 188 mmol) followed by ammonium chloride (1O g, 187 mmol) at rt. The reaction mixture was stirred and warmed to 70 0C for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with chloroform (4 x 100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10 and small amount of triethyl amine) as eluent to give methyl 4-aminothiophene-2-carboxylate (1.8 g, 31%), mp 76-780C. 1H NMR (400 MHz, CDCl3): delta 7.31 (IH, d, JH .6 Hz), 6.40 (IH, d, J=I.6 Hz), 3.85 (3H, s), 3.63 (2H, br s).Further elution of the column with the same solvent system provided methyl 5- aminothiophene-2-carboxylate (0.5 g, 8.5%), mp 70-720C. 1H NMR (400 MHz, CDCl3): delta 7.45 (IH, d, J=4.0 Hz), 6.09 (IH, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s).

Reference： [1]Patent: WO2010/29577,2010,A2 .Location in patent: Page/Page column 38-39

23
[ 527-72-0 ]
[ 14597-58-1 ]
[ 89499-43-4 ]

Yield	Reaction Conditions	Operation in experiment
		Step a:; 4-Nitrothiophene-2-carboxylic acid:; Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10 C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2×50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75%), mp 110-118 C. The product was a mixture of two compounds by HPLC and 1H NMR and was proceeded to the next step.Step b:; Methyl 4-nitrothiophene-2-carboxylate:; To a solution of nitrothiophene-2-carboxylic acids (6.8 g, 39.3 mmol) in methanol (50 mL) was added thionyl chloride (6 mL, 78.6 mmol) drop wise under stirring at rt. The reaction mixture was refluxed for 2 h and attained to rt. The mixture was poured into ice cooled water and stirred for 15 min. The precipitated solid was filtered, washed with cold water and dried to give the product as an off-white solid (6.2 g, 85%). 1H NMR showed that, it is a mixture of two compounds and the crude product was proceded to the next step.; Step c:; Methyl 4-aminothiophene-2-carboxylate:; To a solution of methyl nitrothiophene-2-carboxylates (7 g, 37.43 mmol) in a mixture of water (150 mL) and methanol (50 mL) was added Conc. hydrochloric acid (4.5 mL). To the above solution was added iron powder (10.5 g, 188 mmol) followed by ammonium chloride (10 g, 187 mmol) at rt. The reaction mixture was stirred and warmed to 70 C. for 1 h and was then allowed to cool to rt. The solution was filtered and basified with saturated sodium bicarbonate solution. The solution was extracted with chloroform (4×100 mL). The combined organic layer was dried over sodium sulfate and filtered. Solvent was evaporated and the residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10 and small amount of triethyl amine) as eluent to give methyl 4-aminothiophene-2-carboxylate (1.8 g, 31%), mp 76-78 C. 1H NMR (400 MHz, CDCl3): delta 7.31 (1H, d, J=1.6 Hz), 6.40 (1H, d, J=1.6 Hz), 3.85 (3H, s), 3.63 (2H, br s). Further elution of the column with the same solvent system provided methyl 5-aminothiophene-2-carboxylate (0.5 g, 8.5%), mp 70-72 C. 1H NMR (400 MHz, CDCl3): delta 7.45 (1H, d, J=4.0 Hz), 6.09 (1H, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s).

Reference： [1]Patent: US2010/68178,2010,A1 .Location in patent: Page/Page column 16-17

24
[ 14597-58-1 ]
C₁₄H₁₅ClO [ No CAS ]
[ 1117680-98-4 ]

Yield	Reaction Conditions	Operation in experiment
		(1) Methyl 5-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carboxamido]thiophene-2-carboxylate [Show Image] A suspension of 5,6,6a,7,8,9-hexahydro-4H-2-phenalenecarboxylic acid (0.100 g) in anhydrous benzene (3 ml) was added with thionyl chloride (1 ml), and the mixture was refluxed by heating for 3 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in anhydrous benzene (2 ml) and pyridine (2 ml), the solution was added with methyl 5-amino-thiophene-2-carboxylate (0.076 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 10% aqueous sodium carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane = 1:15) to obtain the title compound (0.094 g, yield: 57%). The compound was recrystallized from chloroform-n-hexane to obtain colorless needles (melting point: 188-189C). 1H-NMR (400MHz, CDCl3): delta 1.34 (2H, td, J=12.0, 3.9Hz), 1.72-1.85 (2H, m), 1.87-2.04 (4H, m), 2.52-2.63 (1H, m), 2.80-2.85 (4H, m), 3.87 (3H, s), 6.75 (1H, d, J=4.2Hz), 7.41 (2H, s), 7.64 (1H, d, J=4.2Hz), 8.94 (1H, br-s)
	With pyridine; dmap; In benzene; at 20℃; for 15h;	General procedure: To a suspension of 5,6,6a,7,8,9-hexahydro-4H-phenalene-2-carboxylic acid (0.338 g, 1.56 mmol) in benzene (7.5 ml) was added SOCl2 (2.5 ml). The reaction mixture was refluxed for 4 h, then evaporated, and the residue was dissolved in benzene (3 ml) and pyridine (10 ml). Methyl 4-aminobenzoate (0.259 g, 1.71 mmol) and 4-DMAP (0.020 g, 0.164 mmol) were added to the resulting solution. The reaction mixture was stirred at rt for 15 h, then poured into 2 M aqueous HCl and extracted with AcOEt. The organic phase was washed with 10% aqueous Na2CO3. Usual work-up gave a residue, which was purified by silica gel column chromatography(AcOEt/n-hexane = 1:10) to afford methyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carboxamido]benzoate (0.478 g,88%). To a suspension of the above ester (0.385 g, 1.10 mmol) in EtOH (10 ml) was added 2 M aqueous NaOH (7.5 ml). The reaction mixture was stirred at 60 C for 1 h, then cooled, acidified by adding 2 M aqueous HCl and extracted with CHCl3. Usual work-up gave a residue, which was purified by recrystallization from EtOH to afford 7a (0.348 g, 94%).

Reference： [1]Patent: EP2189443,2010,A1 .Location in patent: Page/Page column 18
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4342 - 4350

25
[ 14597-58-1 ]
C₁₅H₁₇ClO [ No CAS ]
[ 1117681-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap; In benzene;	(1) Methyl 5-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carboxamido]thiophene-2-carboxylate [Show Image] A suspension of 6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenecarboxylic acid (0.110 g) in anhydrous benzene (3 ml) was added with thionyl chloride (1 ml), and the mixture was refluxed by heating for 3 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in anhydrous benzene (2 ml) and pyridine (2 ml), the solution was added with methyl 5-amino-thiophene-2-carboxylate (0.079 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 10% aqueous sodium carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane = 1:15) to obtain the title compound (0.109 g, yield: 62%). The compound was recrystallized from chloroform-n-hexane to obtain colorless needles (melting point: 179-180C). 1H-NMR (400MHz, CDCl3): delta 1.15 (3H, s), 1.49 (2H, td, J-12.9, 5.1Hz), 1.69 (2H, dt, J=12.9, 3.9Hz), 1.76-1.87 (2H, m), 1.97-2.12 (2H, m), 2.73-2.84 (2H, m), 2.88-2.96 (2H, m), 3.86 (3H, s), 6.76 (1H, d, J=4.2Hz), 7.39 (2H, s), 7.63 (1H, d, J=4.2Hz), 9.09 (1H, br-s)
	With pyridine; dmap; In benzene; at 20℃; for 15h;	General procedure: To a suspension of 5,6,6a,7,8,9-hexahydro-4H-phenalene-2-carboxylic acid (0.338 g, 1.56 mmol) in benzene (7.5 ml) was added SOCl2 (2.5 ml). The reaction mixture was refluxed for 4 h, then evaporated, and the residue was dissolved in benzene (3 ml) and pyridine (10 ml). Methyl 4-aminobenzoate (0.259 g, 1.71 mmol) and 4-DMAP (0.020 g, 0.164 mmol) were added to the resulting solution. The reaction mixture was stirred at rt for 15 h, then poured into 2 M aqueous HCl and extracted with AcOEt. The organic phase was washed with 10% aqueous Na2CO3. Usual work-up gave a residue, which was purified by silica gel column chromatography(AcOEt/n-hexane = 1:10) to afford methyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carboxamido]benzoate (0.478 g,88%). To a suspension of the above ester (0.385 g, 1.10 mmol) in EtOH (10 ml) was added 2 M aqueous NaOH (7.5 ml). The reaction mixture was stirred at 60 C for 1 h, then cooled, acidified by adding 2 M aqueous HCl and extracted with CHCl3. Usual work-up gave a residue, which was purified by recrystallization from EtOH to afford 7a (0.348 g, 94%).

Reference： [1]Patent: EP2189443,2010,A1 .Location in patent: Page/Page column 33
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 4342 - 4350

26
[ 14597-58-1 ]
methyl 2,4-dioxo-4-(thiophen-2-yl)butanoate [ No CAS ]
[ 1228095-80-4 ]

Reference： [1]Journal of Combinatorial Chemistry,2010,vol. 12,p. 510 - 517

27
[ 14597-58-1 ]
[ 2009-81-6 ]
methyl 5-formylthieno[2,3-b]pyridine-2-carboxylate [ No CAS ]

Reference： [1]Synthesis,2010,p. 2767 - 2770

28
[ 14597-58-1 ]
C₂₀H₂₅N₄O₂PolS [ No CAS ]
C₂₇H₃₀N₅O₅PolS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of 350 mg (2.23 mmol) <strong>[14597-58-1]methyl 5-amino-2-thiophenecarboxylate</strong> in 10mL of anhydrous dichloromethane was added 448 mg (2.23 mmol) A- nitrobezenechloroformate. The reaction mixture was stirred at room temperature for half an hour and concentrated. Diisopropylethylamine (1.09 mL, 6.22 mmol), DMHB resin bound Lambda/-[(2-methylimidazo[2,1-jb][1 ,3]thiazol-6-yl)methyl]-L-tyrosinamide(300 mg, 0.24 mmol) 6 and dimethyl formamide (10 mL) were added to reaction mixture and shaked overnight. The resin was washed with CH2CI2 (3 x 10 mL), C^C^/MeOH (1 :1 , 3 x 10 mL), MeOH (3 x 10 mL) and CH2CI2 (3 x 1OmL). The resulting resin was dried in vacuum oven at 35 0C for 24 h.

Reference： [1]Patent: WO2006/65788,2006,A2 .Location in patent: Page/Page column 7; 8; 10; 11

29
[ 331005-35-7 ]
[ 14597-58-1 ]
[ 1314091-73-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

30
[ 14597-58-1 ]
C₁₄H₁₀F₂N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

31
[ 14597-58-1 ]
C₁₄H₉ClF₂N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

32
[ 14597-58-1 ]
[ 1254834-90-6 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

33
[ 14597-58-1 ]
C₁₃H₁₄N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

34
[ 14597-58-1 ]
C₁₅H₁₄N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

35
[ 14597-58-1 ]
[ 1195774-95-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

36
[ 14597-58-1 ]
C₁₄H₁₁ClN₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

37
[ 14597-58-1 ]
[ 1195774-33-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

38
[ 14597-58-1 ]
C₁₃H₁₄N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

39
[ 14597-58-1 ]
C₁₅H₁₄N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

40
[ 14597-58-1 ]
C₁₄H₁₂N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

41
[ 14597-58-1 ]
C₁₄H₁₁ClN₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

42
[ 14597-58-1 ]
[ 1314090-94-2 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

43
[ 14597-58-1 ]
C₁₃H₁₁F₃N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

44
[ 14597-58-1 ]
C₁₅H₁₁F₃N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

45
[ 14597-58-1 ]
C₁₄H₉F₃N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

46
[ 14597-58-1 ]
C₁₄H₈ClF₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

47
[ 14597-58-1 ]
[ 1195774-46-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

48
[ 14597-58-1 ]
C₁₃H₁₁F₃N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

49
[ 14597-58-1 ]
C₁₅H₁₁F₃N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

50
[ 14597-58-1 ]
C₁₄H₉F₃N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

51
[ 14597-58-1 ]
C₁₄H₈ClF₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

52
[ 14597-58-1 ]
[ 1195774-47-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

53
[ 14597-58-1 ]
C₁₃H₁₁F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

54
[ 14597-58-1 ]
C₁₅H₁₁F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

55
[ 14597-58-1 ]
C₁₄H₉F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

56
[ 14597-58-1 ]
C₁₄H₈ClF₃N₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

57
[ 14597-58-1 ]
[ 1195774-53-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

58
[ 14597-58-1 ]
C₁₃H₁₁F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

59
[ 14597-58-1 ]
C₁₅H₁₁F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

60
[ 14597-58-1 ]
C₁₄H₉F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

61
[ 14597-58-1 ]
C₁₄H₈ClF₃N₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

62
[ 14597-58-1 ]
[ 1314091-03-6 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

63
[ 14597-58-1 ]
C₁₃H₁₄N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

64
[ 14597-58-1 ]
C₁₅H₁₄N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

65
[ 14597-58-1 ]
C₁₄H₁₂N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

66
[ 14597-58-1 ]
C₁₄H₁₁ClN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

67
[ 14597-58-1 ]
[ 1314091-06-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

68
[ 14597-58-1 ]
C₁₉H₁₈N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

69
[ 14597-58-1 ]
C₂₁H₁₈N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

70
[ 14597-58-1 ]
C₂₀H₁₆N₂O₃S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

71
[ 14597-58-1 ]
C₂₀H₁₅ClN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

72
[ 14597-58-1 ]
[ 1314091-12-7 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

73
[ 14597-58-1 ]
C₁₆H₁₅N₃O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

74
[ 14597-58-1 ]
C₁₄H₉F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

75
[ 14597-58-1 ]
C₁₃H₇F₃N₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

76
[ 14597-58-1 ]
C₁₃H₆ClF₃N₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

77
[ 14597-58-1 ]
[ 1314091-39-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

78
[ 14597-58-1 ]
C₁₂H₁₁FN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

79
[ 14597-58-1 ]
C₁₂H₁₁ClN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

80
[ 14597-58-1 ]
[ 1314092-16-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

81
[ 14597-58-1 ]
C₁₃H₉FN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

82
[ 14597-58-1 ]
C₁₃H₈ClFN₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

83
[ 14597-58-1 ]
[ 1314091-16-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713
[3]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

84
[ 14597-58-1 ]
C₁₄H₁₁FN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

85
[ 14597-58-1 ]
methyl 5-(4-chloro-2-methyl-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

86
[ 14597-58-1 ]
C₁₃H₉ClN₂O₂S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

87
[ 14597-58-1 ]
C₁₃H₈Cl₂N₂OS [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

88
[ 14597-58-1 ]
[ 1314091-22-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 708 - 713

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P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
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

[ CAS No. 14597-58-1 ] {[proInfo.proName]}

Quality Control of [ 14597-58-1 ]

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[ 14597-58-1 ] Synthesis Path-Upstream 1~8

[ 14597-58-1 ] Synthesis Path-Downstream 1~88

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[ 14597-58-1 ]