[ CAS No. 154992-24-2 ] {[proInfo.proName]}

Name: 154992-24-2|4-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile|98%
Brand: Ambeed
SKU: A108339
Price: 5.0 USD
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2D 3D

Structure of 154992-24-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 154992-24-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 154992-24-2 ]

SDS Specification

Alternatived Products of [ 154992-24-2 ]

Product Details of [ 154992-24-2 ]

CAS No. :	154992-24-2	MDL No. :	MFCD00925776
Formula :	C₁₇H₁₈F₃N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ARBYGDBJECGMGA-UHFFFAOYSA-N
M.W :	369.34	Pubchem ID :	132981
Synonyms :	HMR-3841;PSK-3841

Calculated chemistry of [ 154992-24-2 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.47
Num. rotatable bonds :	6
Num. H-bond acceptors :	7.0
Num. H-bond donors :	1.0
Molar Refractivity :	93.64
TPSA :	84.64 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.9
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	3.29
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	2.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.23
Solubility :	0.219 mg/ml ; 0.000592 mol/l
Class :	Soluble
Log S (Ali) :	-3.51
Solubility :	0.115 mg/ml ; 0.000311 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.41
Solubility :	0.0145 mg/ml ; 0.0000394 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.7

Safety of [ 154992-24-2 ]

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 [ 154992-24-2 ]

* 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 [ 154992-24-2 ]
Downstream synthetic route of [ 154992-24-2 ]

[ 154992-24-2 ] Synthesis Path-Upstream 1~6

1
[ 154992-24-2 ]
[ 13248-54-9 ]
[ 4427-97-8 ]

Reference： [1] Patent: US6242611, 2001, B1,

2
[ 4753-59-7 ]
[ 143782-20-1 ]
[ 154992-24-2 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 27, p. 14143 - 14148

3
[ 4753-59-7 ]
[ 143782-20-1 ]
[ 154992-24-2 ]

Reference： [1] Patent: US6107488, 2000, A,

4
[ 654-70-6 ]
[ 154992-24-2 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 27, p. 14143 - 14148

5
[ 1259327-69-9 ]
[ 154992-24-2 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 27, p. 14143 - 14148

6
[ 208122-09-2 ]
[ 154992-24-2 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 27, p. 14143 - 14148

[ 154992-24-2 ] Synthesis Path-Downstream 1~13

1
[ 112-64-1 ]
[ 154992-24-2 ]
RU 58841-myristate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.2%	With triethylamine; In chloroform; for 24h;	EXAMPLE 1 Preparation of the Compound of the Formula II [0051] 300 mg of 4-[3-(4-hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl]-2-(trifluoro-methyl)benzonitrile, compound 1 hereinafter, (8.13×10-4 mol) were reacted with 400 mg of myristoyl chloride (1.62×10-3 mol) in the presence of 0.5 ml of triethylamine in 10 ml of absolute chloroform with stirring for 24 hours (h). After completion of the reaction, the formation of a lipophilic product was observed by a TLC check (silica gel plate, eluant ethyl acetate). A Chromatotron was used (methylene chloride as eluant) for quantitative removal of the presumed ester. The organic solution of the removed reaction product was evaporated, recrystallized with water from methanol/chloroform and dried. The compound of the formula II was identified on the basis of 1H NMR (400 MHz) spectroscopy, mass spectroscopy and C-H-N analysis, and 13C NMR, and H-H and C-H Cosy spectra: [0052] 1H-NMR (CDCl3; 400,132 MHz, ppm): 0.88 (m, 3 H, CH3); 1.25 (m, 20 H, CH2); 1.54 (s, 6 H, CH3); 1.69-1.81 (m, 6 H, CH2); 2.30 (m, 2 H, CH2); 3.39 (m, 2 H, CH2); 4.13 (m, 2 H, CH2); 7.91 (d, 1 H, ar); 8.01 (d, 1 H, ar); 8.16 (s, 1 H, ar). [0053] 13C-NMR (CDCl3; 100,625 MHz): distinct signals at ppm: 14.12; 22.69; 23.51; 25.0; 26.15; 26.30; 29.18; 29.28; 29.36; 29.48; 29.61; 29.65; 29.68; 31.93; 34.32; 40.0; 61.87; 63.34; 1208.25; 115.02; 122.89; 122.94; 122.97; 123.04; 123.35; 127.85; 135.27; 136.50; 152.85; 173.67; 174.56. [0054] The melting point of the compound of the formula II is 70.7 C. to 72.4 C. [0055] The yield was 260 mg (4.49×10-4 mol). This corresponds to a yield of 55.2%. [0056] Mass spectrum MS: 579.7 [TABLE-US-00001] Molecular composition: C 64.23%; H 7.65%; F 9.83%; N 7.25%; O 11.04% [0057] CHN analysis: [TABLE-US-00002] Atom Theoret. value 1st Measurement 2nd Measurement C 64.23 63.97 63.86 H 7.651 7.706 7.945 N 7.249 6.942 7.029

Reference： [1]Patent: US2003/229129,2003,A1 .Location in patent: Page 5

2
toluene ethanol [ No CAS ]
[ 4753-59-7 ]
[ 143782-20-1 ]
[ 154992-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; methanol; ethanol; dichloromethane; water;	EXAMPLE 4 4-(4,4-dimethyl-2,5-dioxo-3-(4-hydroxybutyl) 1-imidazolidinyl)-2-(trifluoromethyl)-benzonitrile 300 ml of dimethylformamide and 100 g of the product of Example 3 are introduced at 20/22 C. and the reaction medium is maintained under agitation at this temperature for approximately 5 minutes then 98.5 g of 4-bromobutyl acetate then 20 g of soda are added and the whole is maintained under agitation and under a nitrogen atmosphere at +20/+22 C. for approximately 22 hours. While maintaining agitation, at this temperature, 20 g of soda is added then over approximately 5 minutes 400 ml of methanol is added and the whole is maintained in this way for 1 hour. While leaving the temperature to rise, 500 ml of demineralized water at +20 C. is introduced under agitation, then the reaction medium is placed under agitation, 500 ml of demineralized water is added at +20 C. and the whole is maintained under agitation for 1 hour at 25/30 C., then cooled down under agitation to +0/+5 C., and maintained for 2 hours, followed by separating, washing with 4100 ml of demineralized water and drying. Purification is carried out by adding 696 ml of methylene chloride at 20/22 C. and washing with 3232 ml of demineralized water then drying, 5.8 g of supra black is added, the medium is maintained under agitation at 20+-2 C. for 2 hours followed by filtering and rinsing with 2116 ml of methylene chloride. After concentrating under agitation, 116 ml of denat. ethanol toluene is added at 20 C. then 174 ml of demineralized water is added. The reaction medium is cooled down under agitation to 20/22 C., maintained under agiatation for 2 hours at this temperature then cooled down to 0+-2 C. and maintained for 1 hour under these conditions, followed by separating, washing with 258 ml of ethanol with 50% water at 0/+2 C. and drying. In this way 111.5 g of expected product (white powder) is obtained. M.p.=102 C.

Reference： [1]Patent: US6107488,2000,A

Yield	Reaction Conditions	Operation in experiment
		9.9 ml of 4-chloro-1-butanol and 24.3 g of imidazole were stirred in 50 ml of tetrahydrofuran. 2.82 g of terbutyldimethylsilyl chloride in 20 ml of tetrahydrofuran were added dropwise at a temperature below 20 C. The mixture was stirred for 18 hours at ambient temperature, followed by separating, rinsing with tetrahydrofuran and the solvent was eliminated under reduced pressure. The residue was purified by chromatography on silica (eluant: cyclohexane-ethyl acetate (95-5)) to obtain 17.5 g of the expected product.

4
[ 288-32-4 ]
sodium thiosulfate [ No CAS ]
[ 603-35-0 ]
[ 154992-24-2 ]
[ 192805-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; In dichloromethane;	STAGE 1: 4-(4,4-dimethyl-2,5-dioxo-3-(4-iodobutyl)-1-imidazolidinyl)-2-(trifluoromethyl)-benzonitrile 787 mg of triphenyl phosphine, 204 mg of imidazole, 762 mg of iodine and 5 ml of methylene chloride are introduced, the suspension is agitated for 45 minutes at ambient temperature, then over about 3 minutes, 1.1 g of <strong>[154992-24-2]4-(4,4-dimethyl-2,5-dioxo-3-(4-hydroxybutyl)-1-imidazolidinyl)-2-(trifluoromethyl)-benzonitrile</strong> obtained in Example 1 of EP 0,580,459 in 7 ml of methylene chloride is added. Rinsing is carried out with 1 ml of methylene chloride followed by agitation for 4 hours at ambient temperature. The insoluble part is separated off, rinsed with methylene chloride, the organic phase is washed with a saturated aqueous solution of sodium thiosulphate then with salt water and dried. Chromatography is carried out on silica eluding with methylene chloride-ethyl acetate: 97-3. After crystallization from ether, 1.26 g of expected product (white crystals) is obtained. M.p.=87-88 C.

Reference： [1]Patent: US6242611,2001,B1

5
water+ice [ No CAS ]
[ 108-23-6 ]
[ 154992-24-2 ]
[ 6482-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-(Dimethylamino)pyridine; sodium chloride; In pyridine; toluene;	EXAMPLE 1 4-(3-(4-cyano-3-(trifluoromethyl)-phenyl)-5,5-dimethyl-2,4-dioxo-1-imidazolidinyl)butyl and 1-methylethyl carbonate 0.369 g of <strong>[154992-24-2]4-(4,4-dimethyl-2,5-dioxo-3-(4-hydroxybutyl)-1-imidazolidinyl)-2-(trifluoromethyl)-benzonitrile</strong> obtained in Example 1 of EP 0,580,459 and 24 ml of dimethylaminopyridine in solution in 3.5 mg of pyridine dried over potash are introduced, the whole is cooled down to 0 C. and 2 ml of a toluenic solution of 1 M isopropyl chloroformate is added. After 2 hours 15 minutes of agitation, the reaction medium is poured into 30 g of water+ice and extracted with ether. The ethereal phases are combined, washed with a saturated solution of sodium chloride and dried. The oil obtained is taken up in toluene and evaporation to dryness is carried out under reduced pressure. After chromatography on silica, eluding with methylene chloride-ethyl acetate: 100-3, 0.413 g of expected product (white crystals) is obtained. M.p.=82 C.

Reference： [1]Patent: US6242611,2001,B1

6
[ 154992-24-2 ]
[ 13248-54-9 ]
[ 4427-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap;	EXAMPLE 2 4-[3-[4-cyano-3-(trifluoromethyl) phenyl]-5,5-dimethyl-2,4-dioxo-1-imidazolidinyl] butyl and cyclohexyl carbonate The operation is carried out as in Example 1, starting with 740 mg of <strong>[154992-24-2]4-(4,4-dimethyl-2,5-dioxo-3-(4-hydroxybutyl)-1-imidazolidinyl)-2-(trifluoromethyl)-benzonitrile</strong> obtained in Example 1 of EP 0,580,459, 48 mg of 4-dimethylaminopyridine and 7 ml of pyridine, the whole is cooled down to 10 C.+-2 C. and 650 mg of cyclohexyl chloroformate is added. The operation is continued as in Example 1 and after chromatography on silica, eluding with methylene chloride-ethyl acetate: 97-3, 948 mg of expected product is obtained. M.p.=121-122 C.

Reference： [1]Patent: US6242611,2001,B1

7
[ 4753-59-7 ]
[ 143782-20-1 ]
[ 154992-24-2 ]