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[ CAS No. 152459-95-5 ] {[proInfo.proName]}

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Chemical Structure| 152459-95-5
Chemical Structure| 152459-95-5
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Kwangwoon Lee ; Marco Barone ; Amanda L. Waterbury , et al. DOI: PubMed ID:

Abstract: Biochemical crosstalk between two or more histone modifcations is often observed in epigenetic enzyme regulation, but its functional signifcance in cells has been difcult to discern. Previous enzymatic studies revealed that Lys14 acetylation of histone H3 can inhibit Lys4 demethylation by lysine-specifc demethylase 1 (LSD1). In the present study, we engineered a mutant form of LSD1, Y391K, which renders the nucleosome demethylase activity of LSD1 insensitive to Lys14 acetylation. K562 cells with the Y391K LSD1 CRISPR knockin show decreased expression of a set of genes associated with cellular adhesion and myeloid leukocyte activation. Chromatin profling revealed that the cis-regulatory regions of these silenced genes display a higher level of H3 Lys14 acetylation, and edited K562 cells show diminished H3 mono-methyl Lys4 near these silenced genes, consistent with a role for enhanced LSD1 demethylase activity. These fndings illuminate the functional consequences of disconnecting histone modifcation crosstalk for a key epigenetic enzyme.

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Product Details of [ 152459-95-5 ]

CAS No. :152459-95-5 MDL No. :MFCD05662257
Formula : C29H31N7O Boiling Point : -
Linear Structure Formula :- InChI Key :KTUFNOKKBVMGRW-UHFFFAOYSA-N
M.W : 493.60 Pubchem ID :5291
Synonyms :
STI571;CGP-57148B
Chemical Name :N-(4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide

Calculated chemistry of [ 152459-95-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 37
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.24
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 154.5
TPSA : 86.28 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.04
Log Po/w (XLOGP3) : 3.52
Log Po/w (WLOGP) : 3.49
Log Po/w (MLOGP) : 2.15
Log Po/w (SILICOS-IT) : 3.69
Consensus Log Po/w : 3.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.07
Solubility : 0.0042 mg/ml ; 0.00000851 mol/l
Class : Moderately soluble
Log S (Ali) : -5.02
Solubility : 0.00476 mg/ml ; 0.00000964 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -9.67
Solubility : 0.000000105 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.78

Safety of [ 152459-95-5 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P201-P202-P260-P263-P264-P270-P280-P308+P313-P405-P501 UN#:N/A
Hazard Statements:H341-H351-H360-H362 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 152459-95-5 ]

* 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 [ 152459-95-5 ]

[ 152459-95-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 109-01-3 ]
  • [ 404844-11-7 ]
  • [ 152459-95-5 ]
YieldReaction ConditionsOperation in experiment
97.52% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4.5h; 200 g of the compound 4-chloromethyl-N- [4-methyl-3- (4-pyridin-3-pyrimidin-2-amino) phenyl] benzamide was added to1.8 L of N, N-dimethylformamide,86.9 g of potassium carbonate (d (0.5) was 20 mum) and 51 g of N-methylpiperidine were added with stirring,80 reaction,4.5 hours TLC detection reaction was complete,Drop to room temperature,Add 10.8L of purified water,filter,dry,Get 228.9g crude imatinib, the yield of 99.2%Purity 98.76%.Refined imatinib crude:228.5 g of imatinib obtained was added to 800 ml of ethanol,Reflux dissolved,Cooled to 0 ~ 5 ,filter,dry,Get imatinib 224.3g,Yield 97.52%.
91% In 1,4-dioxane; at 135℃; for 3h;Conversion of starting material; Example 9 A flask containing a mixture of 4-chloromethyl-N-{4-methyl-3- [(4-pyridin-3-yl)pyrimidin-2-ylamino]-phenyl}-benzamide obtained in the previous step (56.072 g; 0.130 M), N-methylpiperazine (84 mL; 75.852 g; 0.757 M) and dioxane (56 mL) was placed in an oil bath at temperature 135C and the reaction mixture was heated for 3 hours. After that time the oil bath was taken away and after cooling the reaction mixture, acetone (150 mL) was added and stirring was continued until the mixture was cooled down to room temperature. The precipitated product was filtered off, washed with cold acetone EPO <DP n="29"/>(50 mL) and dried in the air to afford 59.2 g (yield 91%) of the title compound in the form of a cream-coloured, crystalline solid. M.p. 167-1700C. iH NMR (DMSO-d6): 10.16 (IH, s), 9.27 (IH, d, J=2.2), 8.98 (IH, s), 8.68 (IH, dd, J=4.8-1.6), 8.51 (IH, d, J=5.3), 8.48 (IH, dt, J=8.2-2.0), 8.08 (IH, d, J=I.8), 7.90 (2H, d, J=8.2), 7.45 (5H, m), 7.20 (IH, d, J=8.6), 3.52 (2H, s), 2.35 (8H, m), 2.22 (3H, s), 2.15 (3H,s).
91 - 96% at 120 - 130℃; for 1.5h;Conversion of starting material; Example 10 A flask containing a mixture of 4-chloromethyl-N-{4-methyl-3- [(4-pyridin-3-yl)pyrimidin-2-ylamino]-phenyl}-benzamide (55.276 g; 0.129 M) and N-methylpiperazine (83 mL; 74.949 g; 0.748 M) was placed in an oil bath at temperature 120-1250C and the reaction mixture was heated for 90 minutes. After that time the oil bath was taken away, isopropanol (300 mL) was added to the hot mixture and stirring was continued until the mixture was cooled down to room temperature. The precipitated product was filtered off, washed with cold isopropanol (50 mL) and dried in the air to afford 58.7 g (92%) of the product. Example 11 A flask containing a mixture of 4-chloromethyl-N-{4-methyl-3-[(4-pyridin-3-yl)pyrimidin-2-ylamino]-phenyl}-benzamide (54.953 g; 0.129 M) and N-methylpiperazine (83 mL; 74.949 g; 0.748 M) was placed in an oil bath at temperature 120-1250C and the reaction mixture was heated for 90 minutes. After that time the oil bath was taken away, isopropanol (200 mL) was added to the hot mixture and stirring was continued until the mixture was cooled down to room temperature. The precipitated product was filtered off, washed with a mixture of isopropanol and water (1: 1, 100 mL) and dried in the air to afford 57.7g (91%) of the product. EPO <DP n="30"/>Example 12 A flask containing a mixture of 4-chloromethyl-N-{4-methyl-3- [(4-pyridin-3-yl)pyrimidin-2-ylamino]-phenyl}-benzamide (54.949g; 0.129 M) and N-methylpiperazine (83 mL; 74.949 g; 0.748 M) was placed in an oil bath at temperature 120-1250C and the reaction mixture was heated for 90 minutes. After that time the oil bath was taken away, water (100 mL) was added to the hot mixture and stirring was continued until the mixture was cooled down to room temperature. The precipitated product was filtered off and the residue was taken from the flask with water (80 mL). The whole precipitate was washed with water (3x 100 mL) to afford 60.2g (95%) of the product. Example 13 A flask containing a mixture of 4-chloromethyl-N-{4-methyl-3-[(4-pyridin-3-yl)pyrimidin-2-ylamino]-phenyl}-benzamide (55.00Og; 0.128 M) and N-methylpiperazine (83 mL; 74.949 g; 0.748 M) was placed in a cold oil bath and the reaction mixture was heated until the bath temperature has reached 1300C. Heating at that temperature was continued for 90 minutes. After that time the oil bath was taken away, and when temperature of the reaction mixture dropped to 95C, water (100 mL) was added. Stirring was continued until the mixture was cooled down to room temperature. A solution of sodium hydroxide (5.12g) in water (100 mL) was added and the mixture was stirred for 30 min. The precipitated product was filtered off, washed with water (300 mL) to afford 60.6g (96%) of the product.
89% With calcium carbonate; In N,N-dimethyl-formamide; <strong>[404844-11-7]4-(chloromethyl)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)benzamide</strong>(4) (0.5 g, 1.16 mmol) and 1-methylpiperazine (0.23 g, 2.33 mmol) were reacted with CaCO3 (0.23 g, 2.33mmol) in 5 mL of DMF. The mixture was stirred at 90 oC for 12 h. Thereaction mixture was filtered, and removed the solvent under vacuum. And theresulting solid was washed with water and dried to produce solid with 89% yield (0.51 g, 1.03 mmol). 1HNMR (300 MHz, DMSO) delta 10.16 (s, 1H), 9.27 (d, J = 1.5 Hz, 1H), 8.97(s, 1H), 8.68 (dd, J = 3.3 Hz, 1H), 8.52-8.46 (m,2H), 8.08 (d, J = 1.8 Hz, 1H), 7.90 (d, J =8.4 Hz, 2H), 7.5-7.42 (m, 5H), 7.20 (d, J= 8.4 Hz, 1H), 3.52 (s, 2H), 2.36 (bs, 8H), 2.20 (s, 3H), 2.15(s, 3H). 13C NMR (75 MHz, DMSO): delta165.2, 161.6, 161.2, 159.5, 151.4, 148.2, 142.1, 137.8, 137.2, 134.4, 133.8,132.2, 130.0, 128.6, 127.56 (2C), 123.8, 117.2, 116.7, 107.5, 61.6, 54.7, 52.6,45.7, 17.6. HRMS (ESI) calcd. for C29H32N7O[M+H]+ 494.2668,found 494.2668.
61% In DMF (N,N-dimethyl-formamide); at 20 - 40℃; for 4.25h; Into the reactor 40 L Dimethyl formamide is charged (DMF) into thereactor 19.7 Kgs of N-methyl piperazine is charged. It is stirred for 15 minutes. 13.9Kg of compound of formula (II)is charged to the reaction mass slowly during four hoursat 20-40C. Reaction mass is poured into 400 L DM water and stirred for 15 minutes.Reaction mass is extracted with 3 x 100 L chloroform. All chloroform layers arecombined and washed with 2 x 100 L 5% aq. Sodium hydroxide solution 2 x 100 Lts DMwater. Carbon treatment is given to the chloroform layer. Organic layer Dried oversodium sulfate and distilled off completely under vacuum. 100 Lts Ethyl acetate ischarged to the residue and stirred for 15 minutes at 25-35C. The product of the formula(la)is centrifuged and washed with 40 L Ethyl Acetate. It is dried in oven at 60-70CDrywt. : 9.8 Kg (61%)MR: 202-206C.Purity by HPLC : 99.8%
In N,N-dimethyl-formamide; at -6 - 5℃; for 2h;Product distribution / selectivity; Nu,Nu-Dimethylformamide (250 ml) was added to N-methylpiperazine (1750 ml) and the mixture was cooled to -6C to -1C. 4-Chloromethyl-N-[4-methyl-3-[[4-(3-pyridinyl)-2- pyrimidinyl] amino ]phenyl]benzamide (250 g) was added to the resulting mass at -6C to - 1C and then stirred for 2 hours at -5C to 5C. The reaction mass was quenched into a mixture of water (7 L), ethyl acetate (875 ml) and aqueous ammonia (500 ml) at 20-30C, and the resulting mass was stirred for 3 hours at 20-30C. The resulting solid was filtered and washed with water (1250 ml).[0213] The resulting wet solid (content of 4-methylbenzamide impurity at 2.94 RRt: 1.5% as measured by HPLC) was placed in another reaction flask, followed by the addition of water (2500 ml) and adjusting the pH of the mixture to 3.0 to 4.0 with acetic acid (125 ml). The resulting mixture was filtered through hyflow bed, washed the hyflow bed with water (250 ml) and the resulting aqueous layer was washed with ethyl acetate (1000 ml x 3). The aqueous layer was separated and followed by the addition of ethyl acetate (750 ml) and aqueous ammonia (500 ml) and stirring the resulting mixture for 3 hours at 20-30C. The separated solid was filtered, washed with water (1250 ml) and then dried the material in air oven at 55-65C to give 240 g of crude imatinib free base (Purity by HPLC: 99.7%).Content of Impurities measured by HPLC:1. 4-Methylbenzamide impurity at 2.94 RRt: 0.06%2. '2.24 RRt' impurity: 0.06%3. Formamide impurity at 1.20 RRt: 0.01 %4. Desmethyl impurity at 0.9 RRt: 0.06%.

  • 2
  • [ 152459-95-5 ]
  • [ 130-85-8 ]
  • [ 862366-33-4 ]
YieldReaction ConditionsOperation in experiment
In ethanol; water;Heating / reflux; Example 10; 4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2- pyrimidinyl] amino] phenyl]-benzamide, pamoate; A mixture of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2- pyrimidinyl] amino] phenyl]-benzamide (4.94 g, 10 mmol) and 4, 4'-methylenebis [3-hydroxy-2- naphthoic acid (Fluka, Buchs, Switzerland ; 3.88 g, 10 mmol) in ethanol (50 mL) is heated. Water (25 mL) is then added. Upon cooling, the product crystallises and is filtered-off and dried to afford 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2- pyrimidinyl] amino] phenyl]-benzamide, pamoate as a pale-yellow solid, having the following analytical properties: Analysis found: C, 69.12 ; H, 5.62 ; N, 10.88percent ; H20, 2.50percent. Calculated for C52H47N707-1. 26 H20 : C, 69.04 ; H, 5.52 ; N, 10.84percent ; H20, 2. 51percent.
  • 3
  • [ 581076-59-7 ]
  • [ 66521-66-2 ]
  • [ 152459-95-5 ]
YieldReaction ConditionsOperation in experiment
91% Under nitrogen protection, 40 mg of N,N'-diisopropylselenourea was uniformly mixed with 10 g of chitosan.It was placed in a tubular reactor and calcined at 500 ° C for 5 hours under nitrogen to obtain selenium and nitrogen-doped nano-carbon fibers with selenium promoting large specific surface area. The material was immersed in 0.05 mol/L copper chloride aqueous solution for 18 hours. ,Filtration, washing with water, drying to obtain a catalyst.The above catalyst is determined by ICP, wherein the mass ratio of selenium is 0.01percent, and the mass ratio of copper is 0.12percent;The specific surface area is 28 cc/g.20 mg of the above catalyst with 1.72 g of <strong>[66521-66-2]4-(3-pyridyl)-2-aminopyrimidine</strong> (see I in the following reaction formula)And 4.02g of 4-(N-methylpiperazine)methylbenzoyl (3-bromo-4-methylphenyl)amine (see II in the following reaction formula) were mixed in 20 mL of ethanol under nitrogen protection. Heat at 60 ° C for 3 hours. The catalyst is recovered by centrifugation,Concentrate the supernatant to within 5 mL, that is, a large amount of crystals are precipitated, filtered, and washed with petroleum ether.Imadinib hydrobromide was obtained in a yield of 96percent.Dissolve the salt in 20 mL of water, adjust the pH to 8.7 with 0.2 mol/L NaOH, and extract with ethyl acetate.(3 extractions per 20 mL). The organic phases were combined and dried over anhydrous sodium sulfate. After filtering, the solvent is evaporated.That is, free imatinib was obtained, and the yield was 91percent. ICP analysis indicated that the copper residue in the product was less than 0.03 ppm.
72% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 5.16667h;Inert atmosphere; Reflux; Sonication; To a mixture of 4-(3-pyridyl)-2-pyrimidine-amine (172.2 mg, 1.0 mmol), N-(3-bromo-4-methyl-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide (402.4 mg, 1.0 mmol) and sodium tert.-butylate (144.2 mg, 1.5 mmol) is added a mixture of rac-BINAP (31.2 mg, 0.050 mmol) and Pd2(dba)3*CHCl3 (13 mg, 0.013 mmol) under argon. After addition of 3 ml of xylene the suspension is sonicated for 10 minutes then stirred for 5 hours under reflux. After cooling to room temperature, water (10 ml) is added to the dark brown oil and the product extracted 4 times with methylene chloride (10 ml each). The combined organic extracts are dried over MgSO4 and concentrated in vacuo. The brown oil is purified by flash-chromatography (SiO2, methanol). The product, a pale yellow solid is dissolved in methylene chloride, filtered and concentrated in vacuo. Yield: 484.3 mg of the title compound, 72percent of theory, (99.9percent area by HPLC). The product contains typically roughly 10percent of isomers which can be eliminated by preparative reversed phase chromatography.
71% With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 28h;Inert atmosphere; Autoclave; To 20 L autoclave, 12 (189.4 g, 1.1 mol), 11 (402.3 g, 1 mol), CuI(47.8 g, 0.25 mol), and K2CO3 (276.4 g, 2 mol) were added. Theautoclave was then charged with N2, and a solution of DMEDA(26.8 mL) in 12 L of 1,4-dioxane was slowly dropped. Themixture was mechanically stirred at 100 °C for 28 h. Aftercooling to room temperature, it was poured into a mixture ofconcentrated NH3 (3.5 L) and cold sat. NaCl solution (15 L, 0?5°C) and extracted by EtOAc (3 × 14 L). The combined organiclayer was dried by Na2SO4 and led to white crystal after concentration.The crystal was washed by PE and dried under vacuumovernight to afford 350.5 g of imatinib base 1 in 71percent yield. Mp 207.4?209.2 °C. IR (KBr): 3410, 3290, 2967, 2964, 2932,2801, 1628, 1588, 1532, 1507, 1478, 1450, 1416, 1380, 1346,1007, 829, 761, 700 cm?1. 1H NMR (600 MHz, DMSO-d6, TMS):delta = 10.22 (s, 1 H), 9.30 (d, J = 1.8 Hz, 1 H), 9.02 (s, 1 H), 8.71?8.70(m, 1 H), 8.54?8.50 (m, 2 H), 8.12 (s, 1 H), 7.93 (d, J = 8.4 Hz, 2H), 7.55?7.44 (m, 5 H), 7.23 (d, J = 8.4 Hz, 1 H), 3.53 (s, 2 H),2.53?2.33 (br s, 8 H), 2.25 (s, 3 H), 2.16 (s, 3 H) ppm. 13C NMR(150 MHz, DMSO-d6): delta = 165.3, 161.6, 161.2, 159.4, 151.3,148.1, 142.1, 137.8, 137.2, 134.4, 133.7, 132.2, 130.0, 128.6,127.5, 123.8, 117.2, 116.8, 107.5, 61.6, 54.7, 52.5, 45.7, 17.6ppm. Known compound: CAS Reg. No. 152459-95-5.3
  • 5
  • N-(3-amino-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide [ No CAS ]
  • [ 483324-01-2 ]
  • [ 152459-95-5 ]
YieldReaction ConditionsOperation in experiment
84.5% With acetic acid; In 1,4-dioxane; at 110℃; for 6h;Green chemistry; In a 100 mL single-necked flask,(3-amino-4-methylphenyl) -4- (4-methylpiperazin- 1 -methyl) benzamide (3.0 g, 8.86 mmol)Was dissolved in 1,4-dioxane (30 mL)And then 2-chloro-4- (3-pyridyl) pyrimidine (1.70 g, 8.86 mmol)And glacial acetic acid (20 mL),The temperature was raised to 110 C,Reaction for 6 hours;After completion of the reaction, the system was concentrated under reduced pressure to remove the solvent,Dichloromethane (60 mL) was added,The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution (40 mL x 2)And saturated aqueous sodium chloride (40 mL x 2)Liquid separation,The organic phase was dried over anhydrous sodium sulfate,filter,Concentrated to obtain imatinib 3.7 g,The yield was 84.5%Purity HPLC was greater than 95%.
  • 6
  • [ 109-01-3 ]
  • [ 1072105-05-5 ]
  • [ 66521-66-2 ]
  • [ 152459-95-5 ]
YieldReaction ConditionsOperation in experiment
86% With copper(l) iodide; sodium acetate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; Under nitrogen, 10 mmol of 4- (3-pyridyl) -2-aminopyrimidine (CAS: 66521-66-2)10 mmol of 4-chloromethylbenzoyl (3-bromo-4-methylphenyl) amine (CAS: 1072105-05-5), 10 mmol of N-methylpiperazine (CAS: 109-01-3 ) And 0.2 mmol of cuprous iodide,0.2 mmol of N, N'-diisopropylethylenediamine,110 mmol of sodium acetate in 20 mL of 1,4-dioxane,The reaction was carried out under heating at a temperature of 100 ° C for 4 hours.After completion of the reaction, the solvent was evaporated to dryness with a rotary evaporator and the residue was separated by column chromatography,Obtain 4.2 grams of imatinib in 86percent yield.
  • 7
  • N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide [ No CAS ]
  • [ 66521-66-2 ]
  • [ 152459-95-5 ]
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