[ CAS No. 193537-14-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 193537-14-3 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}	Login		Inquiry

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 193537-14-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 193537-14-3 ]

SDS Specification

Alternatived Products of [ 193537-14-3 ]

Product Details of [ 193537-14-3 ]

CAS No. :	193537-14-3	MDL No. :	MFCD05664039
Formula :	C₁₅H₂₂N₂O₄S	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	XSXVOVXVHBSSSN-UHFFFAOYSA-N
M.W :	326.41	Pubchem ID :	2794740
Synonyms :

Calculated chemistry of [ 193537-14-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.6
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	89.99
TPSA :	110.1 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.4
Log Po/w (XLOGP3) :	2.78
Log Po/w (WLOGP) :	2.28
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	2.74
Consensus Log Po/w :	2.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.134 mg/ml ; 0.00041 mol/l
Class :	Soluble
Log S (Ali) :	-4.75
Solubility :	0.00583 mg/ml ; 0.0000179 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.83
Solubility :	0.482 mg/ml ; 0.00148 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.42

Safety of [ 193537-14-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 193537-14-3 ]

* 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 [ 193537-14-3 ]

[ 193537-14-3 ] Synthesis Path-Downstream 1~17

1
[ 4755-77-5 ]
[ 193537-14-3 ]
[ 474844-00-3 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4443 - 4459

2
[ 79099-07-3 ]
[ 105-56-6 ]
[ 193537-14-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sulfur; triethylamine; In ethanol; for 16.0h;	2-Amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl ester 3-ethyl ester (step a). To a mixture of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (12.9 g), ethyl cyanoacetate (7.345 g), and sulphur (2.080 g) in absolute ethanol (50 mL) was added triethylamine (9 mL). After stirring for 16 h, the precipitate was collected by filtration and washed with ethanol to give the title compound (18.7 g, 88%). 1H NMR (300 MHz, CDCl3): delta 6.02 (s, 2H), 4.31 (s, 2H), 4.23 (q, 2H, J=7.2 Hz), 3.58 (t, 2H, J=6.0 Hz), 2.72-2.80 (brs, 2H), 1.44 (s, 9H), 1.30 (t, 3H, J=7.2 Hz). LC-MS (ESI) m/z 327.0 (M+H).
87%	With sulfur; triethylamine; In ethanol;	General procedure: To a mixture of cyclohexanone (1) (9.80 g, 100 mmol), ethylcyanoacetate (11.32 g, 200.0 mmol), and sulfur (3.20 g, 100.0 mmol) inabsolute ethanol (200 ml) was added triethylamine (20 ml) and refluxedfor 12 h; the reaction mixture was concentrated and the residue waspartitioned between water and ethyl acetate. The organic layer wasseparated, and concentrated, and the crude product was recrystallizedwith ethanol (150 ml), to give 2. Yield 76%, light yellow crystal.
86%	With morpholine; sulfur; In ethanol; at 20℃;	tert-Butyl 4-oxopiperidine-l-carboxylate (101 g, 505 mmol) was dissolved in ethanol (806 mL), and ethyl cyanoacetate (57.2 g, 505 mmol) and sulfur (17.0 g, 531 mmol) were added. The mixture was stirred for a couple of minutes, and then morpholine (44.0 g, 505 mmol) was added. The reaction was stirred at rt overnight. The precipitate was collected by suction filtration and washed with ethanol to yield 142 g (86%) of the title compound.1H-NMR (400 MHz, DMSOd6): delta = 1.25 (t, 3H), 1.41 (s, 9H), 2.63-2.68 (m, 2H), 3.51 (t, 2H), 4.15 (q, 2H), 4.24 (br. s, 2H), 7.32 (s, 2H).LC/MS (method 5): R, = 2.40 min; MS (ESIpos): m/z = 327 [M+H]+.

83%	With sulfur; diethylamine; In ethanol; at 20℃; for 16.0h;	To a 1-Boc-4-piperidone (25.0 g, 123 mmol) in ethanol (100 mL) solution were added ethyl cyanoacetate (14.2 g, 123 mmol, 1 equiv), diethylamine (12.72 mL, 123 mmol, 1 equiv), and sulfur (4.14 g, 129 mmol, 1.05 equiv). The reaction was stirred at room temperature for 16 h then filtered and washed with ethanol (25 mL) to obtain a white solid (33.11 g, 102 mmol, 83%). 1H NMR (DMSO-d6) delta 7.31 (broad s, 2H), 4.22 (s, 2H), 4.13 (q, 2H), 3.49 (t, 2H), 2.63 (t, 2H), 1.39 (s, 9H), 1.23 (t, 3H); LCMS RT=3.49 min, [M+H]+=326.7.
12%	With morpholine; sulfur; In ethanol; at 20 - 40℃;	General procedure: A mixture of the ketone (1 eq.), cyanoacetate (1 eq.), and elemental sulphur (1eq.) in ethanol were combined and heated at 40-70 C. Morpholine or diethylamne (1 eq.) was added dropwise. The reaction was stirred at 40-70 C for 1-4 hours, and then stirred at room temperature overnight. The resulting precipitate was typically collected by filtration and recrystallised from ethanol or toluene.
	With morpholine; sulfur; In ethanol; at 50℃; for 3.0h;	Example 4A 2-Amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl ester 3-ethyl ester To a solution of t-butyl-4-oxo-1-piperidinecarboxylate (25.1 g, 0.13 mol), ethyl cyanoacetate (14.8 mL, 0.14 mol) and sulfur (4.4 g, 0.14 mol) in 200 mL ethanol was added morpholine (30.8 mL, 0.35 mol). The mixture was warmed to 50 C. and stirred for 3 hours. The reaction mixture was then cooled to ambient temperature, diluted with diethyl ether and filtered. The residue was washed with H2O and diethyl ether. The filtrate was concentrated under reduced pressure and purified via column chromatography (SiO2, 70% hexanes:ethyl acetate). The resulting material was combined with the filtration residue to afford the title compound. MS (DCI/NH3) m/z 327 (M+H)+.
	With sulfur; triethylamine; In ethanol; at 20℃; for 16.0h;	The N-(tert-Butoxycarbonyl)-4-piperidone, NCCH2CO2Et and Et3N was mixed at roomtemperature then stirring for 16 h, and then heated to 120 C for 16 h in DMF with the formamidineacetate. Then, the intermediate was reacted with POCl3 and DIPEA in toluene to obtain thecompound 7 (yield 89%).

Reference： [1]Synlett,2010,p. 1351 - 1354
[2]Patent: US2010/120805,2010,A1 .Location in patent: Page/Page column 44
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 7316 - 7326
[4]ChemMedChem,2020,vol. 15,p. 716 - 725
[5]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 2268 - 2279
[6]Patent: WO2009/33581,2009,A1 .Location in patent: Page/Page column 62
[7]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 909 - 926
[8]Journal of Medicinal Chemistry,2012,vol. 55,p. 3101 - 3112
[9]Patent: US2010/298297,2010,A1 .Location in patent: Page/Page column 10; 15
[10]Journal of Medicinal Chemistry,2002,vol. 45,p. 4443 - 4459
[11]Chemical Communications,2013,vol. 49,p. 190 - 192
[12]European Journal of Medicinal Chemistry,2014,vol. 86,p. 270 - 278
[13]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7353 - 7361
[14]Organic and Biomolecular Chemistry,2016,vol. 14,p. 6119 - 6133
[15]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7089 - 7093
[16]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1885 - 1889
[17]Patent: US2009/18114,2009,A1 .Location in patent: Page/Page column 18
[18]MedChemComm,2013,vol. 4,p. 1202 - 1207
[19]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1938 - 1947
[20]Molecules,2016,vol. 21
[21]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1609 - 1613

3
[ 404-72-8 ]
[ 193537-14-3 ]
2-[3-(3-fluoro-phenyl)-thioureido]-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl ester 3-ethyl ester [ No CAS ]