[ CAS No. 155180-53-3 ] {[proInfo.proName]}

Name: 155180-53-3|4-(3-(4-Hydroxybutyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile|97%
Brand: Ambeed
SKU: A106429
Rating: 93 (32 reviews)

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 155180-53-3 * Storage: {[proInfo.prStorage]}

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

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 155180-53-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 155180-53-3 ]

SDS Specification

Alternatived Products of [ 155180-53-3 ]

Product Details of [ 155180-53-3 ]

CAS No. :	155180-53-3	MDL No. :	MFCD00925775
Formula :	C₁₇H₁₈F₃N₃O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FIDNKDVRTLFETI-UHFFFAOYSA-N
M.W :	385.40	Pubchem ID :	197655
Synonyms :		Chemical Name :	4-(3-(4-Hydroxybutyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile

Calculated chemistry of [ 155180-53-3 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.47
Num. rotatable bonds :	6
Num. H-bond acceptors :	6.0
Num. H-bond donors :	1.0
Molar Refractivity :	100.84
TPSA :	99.66 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.91
Log Po/w (XLOGP3) :	2.7
Log Po/w (WLOGP) :	3.45
Log Po/w (MLOGP) :	1.51
Log Po/w (SILICOS-IT) :	4.27
Consensus Log Po/w :	2.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.71
Solubility :	0.076 mg/ml ; 0.000197 mol/l
Class :	Soluble
Log S (Ali) :	-4.45
Solubility :	0.0138 mg/ml ; 0.0000358 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.59
Solubility :	0.00979 mg/ml ; 0.0000254 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.9

Safety of [ 155180-53-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 155180-53-3 ]

* 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 [ 155180-53-3 ]

[ 155180-53-3 ] Synthesis Path-Downstream 1~23

1
[ 155109-08-3 ]
[ 155180-53-3 ]

Yield	Reaction Conditions	Operation in experiment
		77 4-(4,4-dimethyl 3-(4-hydroxybutyl)-5-oxo 2-thioxo-1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile EXAMPLE 77 4-(4,4-dimethyl 3-(4-hydroxybutyl)-5-oxo 2-thioxo-1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile Using the procedure of Example 71, 300 mg of the product of Example 76 were reacted to obtain 236 mg of the expected product melting at 78°-79° C. with a Rf=0.31 (eluant: methylene chloride--acetone (75-25)).

Reference： [1]Current Patent Assignee: Roussel Uclaf - US35956, 1998, E1

2
[ 155180-53-3 ]
[ 1489236-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h 2.1: 1,2-dichloro-ethane; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C 2.2: 17.5 h

Reference： [1]Current Patent Assignee: YALE UNIVERSITY - WO2013/170147, 2013, A1

3
[ 155180-53-3 ]
[ 1108180-97-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dipyridinium dichromate In N,N-dimethyl-formamide for 48h;	14 Example 14: 4-(3-( 4-Cyano-3-( trifluoromethyl)p henyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)butanoic acid RU59063 (145 mg, 0.38 mmol) was dissolved in 2 mL DMF, chargedwith PDC (1.4 g, 3.7 mmol) and stirred for 48 hours, upon which time the mixturewas quenched with 10 mL 1M HCL and extracted into Et20 (5 X 25 mL). The combined organic layers were washed with brine (1 X 100 mL), dried with Na2S04and concentrated down to yield 135 mg (90% yield) pure product. 1H NMR (300MHz, CDCh) o 7.94 (d, J= 8.3, 1H), 7.88 (s, 1H), 7.77 (d, J= 8.2, 1H), 3.82-3.65(m, 2H), 2.50 (s, 2H), 2.14 (s, 2H), 1.59 (s, 6H); 13C NMR (126 MHz, CDCh) o178.6, 177.4, 175.3, 175.2, 137.1, 135.2, 133.5 (q, J = 32.1), 132.1, 127.0 (q, J = 4.7), 121.8 (q, J = 276.2), 114.9, 110.1, 65.2, 43.3, 31.7, 23.1; LRMS (ESI) 421.2(M+Na)+
90%	With dipyridinium dichromate In N,N-dimethyl-formamide for 48h;	1 Example 1: 4-(3-( 4-Cyano-3-( trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)butanoic acid (Ru-Acid) RU59063 ( 4-[3-( 4-hydroxybutyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile; 145 mg, 0.3 8 mmol) was20 dissolved in 2 mL DMF and charged with PDC (1.4 g, 3.7 mmol) and stirred for 48hours, and then the mixture was quenched with 10 mL 1 M HCl and extracted intoEt20 (5 x 25 mL). The combined organic layers were washed with brine (1 x 100mL), dried with NazS04 and concentrated down to yield 135 mg (90% yield) pureproduct. 1H NMR (300 MHz, CDCh) o 7.94 (d, J= 8.3, 1H), 7.88 (s, 1H), 7.77 (d, J25 = 8.2, 1H), 3.82-3.65 (m, 2H), 2.50 (s, 2H), 2.14 (s, 2H), 1.59 (s, 6H); 13C NMR(126 MHz, CDCh) o 178.6, 177.4, 175.3, 175.2, 137.1, 135.2, 133.5 (q, J = 32.1),132.1, 127.0 (q, J= 4.7), 121.8 (q, J= 276.2), 114.9, 110.1, 65.2, 43.3, 31.7, 23.1;LRMS (ESI) 421.2 (M+Na)+.
90%	With dipyridinium dichromate In N,N-dimethyl-formamide for 48h; Inert atmosphere;

90%	With dipyridinium dichromate In N,N-dimethyl-formamide for 48h;	1; 14 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)butanoic acid (Ru-Acid) RU59063 (4-[3-(4-hydroxybutyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile; 145 mg, 0.38 mmol) was dissolved in 2 mL DMF and charged with PDC (1.4 g, 3.7 mmol) and stirred for 48 hours, and then the mixture was quenched with 10 mL 1 M HCl and extracted into Et2O (525 mL). The combined organic layers were washed with brine (1100 mL), dried with Na2SO4 and concentrated down to yield 135 mg (90% yield) pure product. 1H NMR (300 MHz, CDCl3) δ 7.94 (d, J=8.3, 1H), 7.88 (s, 1H), 7.77 (d, J=8.2, 1H), 3.82-3.65 (m, 2H), 2.50 (s, 2H), 2.14 (s, 2H), 1.59 (s, 6H); 13C NMR (126 MHz, CDCl3) δ 178.6, 177.4, 175.3, 175.2, 137.1, 135.2, 133.5 (q, J=32.1), 132.1, 127.0 (q, J=4.7), 121.8 (q, J=276.2), 114.9, 110.1, 65.2, 43.3, 31.7, 23.1; LRMS (ESI) 421.2 (M+Na)+.
33%	Stage #1: [3H]-RU 59063 With dipyridinium dichromate In N,N-dimethyl-formamide for 96h; Stage #2: With dipyridinium dichromate In N,N-dimethyl-formamide for 24h;	4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)butanoic acid 9a To a solution of thiohydantoin alcohol 8a (0.3961 g, 1.03 mmol, 1 equiv) in 4.1 mL DMF was added C18 celite (1.35 g) andpyridinium dichromate (1.35 g, 3.59 mmol, 3.48 equiv). This was stirred 4 d, then additional PDC (0.614 g, 1.63 mmol, 1.58equiv) and C18 celite (0.61 g) were added. The mixture was stirred one additional day, then filtered on celite and rinsed with80 mL of diethyl ether. The filtrate was diluted with 40 mL of water, 1 M aq. HCl was added to achieve a pH < 2, the layerswere separated, and the aqueous layer extracted once more with 40 mL EtOAc. The organic layers were washed separatelywith 40 mL each water and brine, combined, dried over MgSO4, and concentrated. The crude extract was trituratedthoroughly in ether and filtered again on celite, then purified by silica gel flash chromatography with 75-100% EtOAc /hexanes (Rf 0.32, 5% MeOH / 20% acetone / 75% DCM) to afford 0.134 g or 33% yield of 9a. The 1H NMR data in CDCl3agrees with the literature.4 IR νmax (cm-1): 3400 - 3100 (broad), 2931, 2235, 1754, 1711, 1504, 1484, 1433, 1420, 1377,1311, 1279, 1177, 1138. 1H NMR (400 MHz, CDCl3) δ 9.09 - 8.02 (bs, 1H), 7.95 (d, J = 8.3 Hz, 1H), 7.89 (d, J = 2.0 Hz, 1H), 7.76 (dd, J = 8.3, 2.1 Hz, 1H), 3.81 - 3.72 (m, 2H), 2.51 (t, J = 6.9 Hz, 2H), 2.22 - 2.10 (m, 2H), 1.60 (s, 6H). HRMS(ESI) m/z calcd for C17H15O3N3F3S [(M-H)-]: 398.07917, measured: 398.07930.

Reference： [1]Current Patent Assignee: YALE UNIVERSITY - WO2013/170147, 2013, A1 Location in patent: Page/Page column 110
[2]Current Patent Assignee: YALE UNIVERSITY - WO2013/170147, 2013, A1 Location in patent: Page/Page column 96
[3]Gustafson, Jeffrey L.; Neklesa, Taavi K.; Cox, Carly S.; Roth, Anke G.; Buckley, Dennis L.; Tae, Hyun Seop; Sundberg, Thomas B.; Stagg, D. Blake; Hines, John; McDonnell, Donald P.; Norris, John D.; Crews, Craig M. [Angewandte Chemie - International Edition, 2015, vol. 54, # 33, p. 9659 - 9662][Angew. Chem., 2015, vol. 127, p. 9795 - 9798]
[4]Current Patent Assignee: YALE UNIVERSITY - US2016/22642, 2016, A1 Location in patent: Paragraph 0409; 0455
[5]Barrett, Ryan R.G.; Nash, Claire; Diennet, Marine; Cotnoir-White, David; Doyle, Christopher; Mader, Sylvie; Thomson, Axel A.; Gleason, James L. [Bioorganic and Medicinal Chemistry Letters, 2022, vol. 55]

4
[ 155180-53-3 ]
[ 1489236-55-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h 2.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.25 h 2.2: 16 h
	Multi-step reaction with 2 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h / Inert atmosphere 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.25 h / Inert atmosphere 2.2: 16 h / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h 2.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.25 h 2.2: 16 h

Reference： [1]Current Patent Assignee: YALE UNIVERSITY - WO2013/170147, 2013, A1
[2]Gustafson, Jeffrey L.; Neklesa, Taavi K.; Cox, Carly S.; Roth, Anke G.; Buckley, Dennis L.; Tae, Hyun Seop; Sundberg, Thomas B.; Stagg, D. Blake; Hines, John; McDonnell, Donald P.; Norris, John D.; Crews, Craig M. [Angewandte Chemie - International Edition, 2015, vol. 54, # 33, p. 9659 - 9662][Angew. Chem., 2015, vol. 127, p. 9795 - 9798]
[3]Current Patent Assignee: YALE UNIVERSITY - US2016/22642, 2016, A1

5
[ 155180-53-3 ]
[ 1489236-56-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h 2.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.25 h 2.2: 16 h
	Multi-step reaction with 2 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h 2.1: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 0.25 h 2.2: 16 h