[ CAS No. 52560-89-1 ] {[proInfo.proName]}

Name: 52560-89-1|5-(2-Thioxo-2,3-dihydrothiazol-4-yl)thiophene-2-carboxamide|95%
Brand: Ambeed
SKU: A474528
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Quality Control of [ 52560-89-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52560-89-1 ]

SDS Specification

Alternatived Products of [ 52560-89-1 ]

Product Details of [ 52560-89-1 ]

CAS No. :	52560-89-1	MDL No. :	MFCD11040250
Formula :	C₈H₆N₂OS₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AMSLEHALZQXAOV-UHFFFAOYSA-N
M.W :	242.34	Pubchem ID :	4270131
Synonyms :

Calculated chemistry of [ 52560-89-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	60.91
TPSA :	147.45 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	1.42
Log Po/w (WLOGP) :	2.63
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	5.08
Consensus Log Po/w :	2.15

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.563 mg/ml ; 0.00232 mol/l
Class :	Soluble
Log S (Ali) :	-4.12
Solubility :	0.0183 mg/ml ; 0.0000757 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.79
Solubility :	0.396 mg/ml ; 0.00163 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.89

Safety of [ 52560-89-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 52560-89-1 ]

* 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 [ 52560-89-1 ]
Downstream synthetic route of [ 52560-89-1 ]

[ 52560-89-1 ] Synthesis Path-Upstream 1~1

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[ 52560-89-1 ]
[ 68377-92-4 ]

Reference： [1] Patent: US3932400, 1976, A,
[2] Patent: CN107698576, 2018, A,

[ 52560-89-1 ] Synthesis Path-Downstream 1~19

Yield	Reaction Conditions	Operation in experiment
	Bromid III,Ammoniumdithiocarbamat;
	Entspr. Nitrothiophen,entspr. Dithiocarbaminat;

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[ 68377-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; sodium hydroxide;	EXAMPLE 37 2-(3'-t-butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)thiazole. To a solution of 2-mercapto-4-(5'-carbamoyl-2'-thienyl)thiazole, 3.2 g. in 20 ml. of 0.3 % aqueous sodium hydroxide solution, 1-chloro-3-t-butylaminopropanol, 12.64 g. in 20 ml. of methanol was added, while the temperature was maintained at 20C. The reaction solution was stirred at room temperature for 4 hours, and then condensed to a half volume in vacuo. The residual solution, added with 100 ml. of water, was extracted with chloroform. The chloroform extract was washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue, 4.8 g., which was recrystallized from chloroform-light petroleum to yield 2-(3'-t-butylamino-2'-hydroxypropylthio)-4-(5'-carbamoyl-2'-thienyl)thiazole; needles, m.p. 148 - 149C. According to Example 37, the following compounds were synthesised.

Reference： [1]Patent: US3932400,1976,A
[2]Patent: CN107698576,2018,A

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[ 106-89-8 ]
5-[2-[(3-chloro-2-hydroxypropyl)thio]-4-thiazolyl]-2-thiophenecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.19%	With Sodium hydrogenocarbonate In water monomer at 35 - 45℃; for 2h; Large scale;	1.a; 2.a; 3.a; 4.a; 5.a (a) Preparation of Intermediate I: Add 1500 g (6.19 mol) of starting material I to 30 kg of purified water, slowly add 630 g (6.81 mol) of epichlorohydrin; after adding, heat to 40 °C, keep the internal temperature at 35-45 °C and stir for 2 hours; TLC monitoring, after the disappearance of the raw material point After filtering, the filter cake was rinsed with purified water; 2054.5 g (6.14 mol) of intermediate I was obtained by drying under reduced pressure at 50° C., the yield was 99.19%, and the HPLC purity was 99.60%.
93.4%	Stage #1: 5-(2-mercapto-4-thiazolyl)-2-thiophenecarboxamide With Sodium hydrogenocarbonate In tetrahydrofuran; water monomer at 18℃; for 0.8h; Stage #2: 3-chloro-1,2-epoxypropane In tetrahydrofuran; water monomer at 20℃; for 1.5h;	1.1; 2.1; 3.1 (1) Synthesis of 5-[2-[(3-chloro-2-hydroxypropyl)sulfanyl]-4-thiazolyl]-2-thiophenecarboxamide: Add 445 g of tetrahydrofuran (THF) and 100 g of 2-formamide-5-(2-mercapto-1,3-thiazol-4-yl)-thiophene (C181101170-S1) into the reaction kettle, mix and stir, take 500g of water and 34.7g of sodium bicarbonate and mix and stir until all are dissolved.Obtain a sodium bicarbonate solution, and the temperature is lowered to 18°C, the sodium bicarbonate solution was slowly added dropwise to the reaction kettle, and the temperature was controlled at 18°C. The dripping time is 0.8h, 40.1g of epichlorohydrin (C181101170-S2) is slowly dripped into the reactor, the temperature is controlled at 20, and the reaction is stirred for 1.5h. Take 5ml of the solution under stirring and send it to QC for testing.Qualified standard: 2-formamide-5-(2-mercapto-1,3-thiazol-4-yl)-thiophene ≤1.0%, After qualified, proceed to the next step; if not qualified,Extend the reaction time, take samples every 2.4h, Until qualified; transfer the solution into a new reactor,Add 2500g of water dropwise for 1.2h, stir and crystallize at 25 for 1.5h, press filter,The filter cake is rinsed twice with 100g*2 water, filtered by pressure, dried in vacuum, controlled at a temperature of 45, and dried under the condition of a vacuum degree of ≤-0.07MPa to a moisture content of ≤2.0%,Obtain 5-[2-[(3-chloro-2-hydroxypropyl)sulfanyl]-4-thiazolyl]-2-thiophenecarboxamide (intermediate product C181101170-I03),The yield was 93.4%, and the purity was 99.68% as determined by HPLC.
81.27%	With anhydrous zinc chloride In methanol at 62 - 68℃; for 3h;	1 Preparation of 5- [2- [(3-chloro-2-lightopropyl) thio] -4-thiazolyl] -2-thiophenecarboxamide 10 g (41.26 mmol) of 5- (2-spiro-4-thiazolyl) -2-thiophenecarboxamide (Compound II), 4.1 g (44.32 mmol) of epichlorohydrin were added to a 250 ml three-necked reaction flask, Anhydrous zinc chloride 1.5g, anhydrous methanol 200ml, stirring conditions, heating up to 65 ± 3 °C, temperature control reaction of about 3 hours, TLC point board monitoring, until the reaction is complete, the natural cooling to room temperature, filtration, the filtrate under reduced pressure to dry, the intermediate compounds 11.23 g of 5- [2- [(3-chloro-2-hydroxypropyl) thio] -4-thiazolyl] -2-thiophenecarboxamide, the yield was 81.27% and the purity was 99.07%.

Reference： [1]Current Patent Assignee: CHENGDU EASTON BIOPHARMACEUTICALS; SICHUAN QINGMU PHARMACEUTICAL - CN113816949, 2021, A Location in patent: Paragraph 0010; 0034-0038; 0043-0045; 0048-0050; 0053; ...
[2]Current Patent Assignee: SHANDONG CHINA HEALTH BRIDGE PHARMACEUTICAL - CN113061130, 2021, A Location in patent: Paragraph 0124-0126; 0133-0135; 0142-0144
[3]Current Patent Assignee: JIANGXI BAISHEN PHARMACEUTICAL - CN104530033, 2017, B Location in patent: Paragraph 0031; 0032; 0033; 0034

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