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[ CAS No. 86864-60-0 ] {[proInfo.proName]}

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Chemical Structure| 86864-60-0
Chemical Structure| 86864-60-0
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Tian, Gui-Long ; Hsieh, Chia-Ju ; Taylor, Michelle , et al. DOI: PubMed ID:

Abstract: The difference in the secondary binding site (SBS) between the dopamine 2 receptor (D2R) and dopamine 3 receptor (D3R) has been used in the design of compounds displaying selectivity for the D3R versus D2R. In the current study, a series of bitopic ligands based on Fallypride were prepared with various secondary binding fragments (SBFs) as a means of improving the selectivity of this benzamide analog for D3R versus D2R. We observed that compounds having a small alkyl group with a heteroatom led to an improvement in D3R versus D2R selectivity. Increasing the steric bulk in the SBF increase the distance between the pyrrolidine N and Asp110, thereby reducing D3R affinity. The best-in-series compound was (2S,4R)-trans-27 which had a modest selectivity for D3R versus D2R and a high potency in the β-arrestin competition assay which provides a measure of the ability of the compound to compete with endogenous dopamine for binding to the D3R. The results of this study identified factors one should consider when designing bitopic ligands based on Fallypride displaying an improved affinity for D3R versus D2R.

Keywords: Dopamine 2 receptor ; Dopamine 3 receptor ; Fallypride ; Bitopic ligands ; PET imaging

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Product Details of [ 86864-60-0 ]

CAS No. :86864-60-0 MDL No. :MFCD00209550
Formula : C8H19BrOSi Boiling Point : -
Linear Structure Formula :- InChI Key :JBKINHFZTVLNEM-UHFFFAOYSA-N
M.W : 239.23 Pubchem ID :3608067
Synonyms :
Chemical Name :(2-Bromoethoxy)(tert-butyl)dimethylsilane

Calculated chemistry of [ 86864-60-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.39
TPSA : 9.23 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.19
Log Po/w (XLOGP3) : 3.62
Log Po/w (WLOGP) : 3.4
Log Po/w (MLOGP) : 2.69
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 2.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.109 mg/ml ; 0.000457 mol/l
Class : Soluble
Log S (Ali) : -3.5
Solubility : 0.0754 mg/ml ; 0.000315 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.38
Solubility : 0.1 mg/ml ; 0.000419 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.98

Safety of [ 86864-60-0 ]

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

Application In Synthesis of [ 86864-60-0 ]

* 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 [ 86864-60-0 ]

[ 86864-60-0 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 86864-60-0 ]
  • [ 101166-65-8 ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; In N-methyl-acetamide; acetone; PREPARATION 57 4-(1-(2-Hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Hydriodic Acid Salt Combine 2-(t-butyldimethylsilyloxy)ethyl bromide (116.2 g, 486 mmol), and sodium iodide (100 g, 663 mol) in acetone (350 mL) and dimethylformamide (25 mL). Heat to reflux. After 4 hours, cool, filter and evaporate in vacuo to give a residue. Distill the residue to give 2-(t-butyldimethylsilyloxy)ethyl iodide: bp; 60 C. at 0.5 mm Hg.
With sodium iodide; In N-methyl-acetamide; acetone; PREPARATION 57 4-(1-(2-Hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Hydriodic acid salt Combine 2-(t-butyldimethylsilyloxy)ethyl bromide (116.2 g, 486 mmol), and sodium iodide (100 g, 663 mol) in acetone (350 mL) and dimethylformamide (25 mL). Heat to reflux. After 4 hours, cool, filter and evaporate in vacuo to give a residue. Distill the residue to give 2-(t-butyldimethylsilyloxy)ethyl iodide: bp; 60 C. at 0.5 mm Hg.
With sodium iodide; In N-methyl-acetamide; acetone; Preparation 57 4-(1-(2-Hydroxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic Acid Salt Combine 2-(t-butyldimethylsilyloxy)ethyl bromide (116.2 g, 486 mmol), and sodium iodide (100 g, 663 mol) in acetone (350 mL) and dimethylformamide (25 mL). Heat to reflux. After 4 hours, cool, filter and evaporate in vacuo to give a residue. Distill the residue to give 2-(t-butyldimethylsilyloxy)ethyl iodide: bp; 60 C. at 0.5 mm Hg.
With sodium iodide; In acetone; at 70℃; Step 3-A-alternative. J'ert-butyl(2-iodoethoxy)dimethylsilane A solution of (2-bromoethoxy)(tert-butyl)dimethylsilane (500 mg, 0.45 mL, 2.09 mmol) and sodium iodide (470 mg, 3.14 mmol) in 5.0 mL acetone was heated at 70 C with stir overnight. After cooling, solids were removed by filtration and the solid was washed with EtOAc. The combine filtrate and wash was evaporated to give pure title compound. 1H NMR (CDC13, 500 MHz)? 3.85 (t, 6.9 Hz, 2H), 3.22 (t, 7.0 Hz, 2H), 0.93 (s, 9H), 0.11 (s, 6H).

  • 2
  • [ 86864-60-0 ]
  • [ 15944-34-0 ]
  • [ 1033589-07-9 ]
YieldReaction ConditionsOperation in experiment
62% To a solution of 7-chloro-l,8-naphthyridin-2(lH)-one (2.7 g, 15.2 mmol) (J.Org.Chem. 1990, 55, 4744-4750) in N,N-dimethylformamide (4OmL) under nitrogen at O0C was added sodium hydride (0.73 g, 18.3 mmol). The slurry was stirred for ten minutes and then (2- bromoethoxy)-t-butyl dimethylsilane (4.3 g, 18.3 mmol) was added. The mixture was heated at 8O0C for two hours then cooled to room temperature. The reaction mixture was quenched with water and the product extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatography <n="34"/>on silica gel with 20% acetone in n-hexane gave the product as an oil (3.2 g, 62%).MS CES): 338 (MH+) for C16H23N2SiClO21H NMR fDMSO-d): delta ppm -0.00 (s, 6H); 0.81 (s, 9H); 3.91 (t, 2H); 4.53 (t, 2H); 6.80 (d,IH); 7.45 (d, 1 H); 8.06 (d, IH); 8.29 (d, IH).
  • 3
  • [ 50820-65-0 ]
  • [ 86864-60-0 ]
  • [ 1191905-28-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 24h; To a solution of lH-<strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> (3.7 g, 21.2 mmol) and (2- bromoethoxy)(en-butyl)dimethylsilane (5.6 g, 23.3 mmol) in DMF (40 mL) was added K2CO3 (14.6 g, 106 mmol). The mixture was heated to 60 0C for 24 hr then cooled to room temperature and diluted with ethyl acetate (300 ml) and washed with H2O (2 X 200 ml). Then organic layer was dried (MgSO4), filtered and then concentrated to provide 8.2 g of crude methyl l-(2-ethoxy-tert- butyldimethylsilane)-lH-indole-6-carboxylate as an orange brown oil.
  • 4
  • [ 40711-33-9 ]
  • [ 86864-60-0 ]
  • [ 1192313-38-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In N,N-dimethyl-formamide; at 0 - 60℃; To a suspension of ethyl 5-oxo-2,5-dihydro-1 H-pyrazole-3-carboxylate (1.5 g, prepared with an analogous procedure to that described in Preparation 1 ) and Na2CO3 (1.22 g) in dry DMF (20 ml_), [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (1.11 ml.) was added drop wise and the mixture was stirred at 60 0C overnight. The reaction mixture was cooled down to rt and filtered to remove the Na2CO3. The filtrate was diluted with DMF and Na2CO3 (1.22g) and [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (2.1 ml.) were added and the mixture was stirred at 60 0C for additional 36h. After cooling, the mixture was diluted with Et2O, washed with chilly water, dried, filtered and evaporated under reduced pressure. The crude was dissolved in DCM (15 ml.) and 2,6-lutidine (1.08 ml.) and [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (0.86 ml.) were added at 0 0C and the mixture was stirred at rt for 1 h. The mixture was diluted in DCM, washed with NaHCO3sat and then with HCI 0.25N. The organic layer was dried and the solvent evaporated under reduced pressure. The crude was purified by flash chromatography on silica column eluting with Cy/AcOEt with a gradient of Cy from 100% to 80% to give the title compound as colourless oil (0.63 g).MS (m/z): 315 [MH]+.
  • 5
  • [ 1370261-96-3 ]
  • [ 86864-60-0 ]
  • [ 1439909-16-6 ]
YieldReaction ConditionsOperation in experiment
38% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 20.0℃; for 72.0h; 4-(3-(2H-1,2,3-Triazol-2-yl)phenylamino)-2-((lR,2S)-2- aminocyclohexylamino)pyrimidine-5 -carboxamide was prepared by the same scheme shown in Example 1 for 4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-2-((1S,2R)-2- aminocyclohexylamino)pyrimidine-5-carboxamide. 4-(3-(2H-1,2,3-Triazol-2-yl)phenylamino)- 2-((1R,2S)-2-aminocyclohexylamino)pyrimidine-5-carboxamide (230 mg, 0.58 mmol) was dissolved in 6 mL NMP. To it were added DIEA (300 xL, 1.74 mmol) and (2-bromoethoxy)(tert- butyl)dimethylsilane (500 mu, 2.32 mmol). The mixture was stirred at RT for three days. It was diluted with 200 mL EtOAc, washed with brine three times, dried, concentrated and subjected to flash column to isolate 4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-2-((1R,2S)-2-(2-(tert- butyldimethylsilyloxy)ethylamino)cyclohexylamino)pyrimidine-5-carboxamide (120 mg, 38%). It was dissolved in 10 mL THF and treated with B^NF (l.OM in THF, 0.66 mL, 0.66 mmol) for 40 m. The mixture was concentrated in vacuo, acidized with TFA and subjected to reverse phase preparative HPLC to isolate the title compound (85 mg). MS found for C21H27N902 as (M+H)+ 438.4. UV: lambda=249 nm.
  • 6
  • [ 13395-85-2 ]
  • [ 86864-60-0 ]
  • C18H31ClO2Si [ No CAS ]
  • 7
  • [ 20637-09-6 ]
  • [ 86864-60-0 ]
  • methyl 4-(4-((2-((tert-butyldimethylsilyl)oxy)ethyl)amino)phenyl)butanoate [ No CAS ]
  • 8
  • [ 20637-09-6 ]
  • [ 86864-60-0 ]
  • C20H35NO3Si [ No CAS ]
  • 9
  • [ 13659-23-9 ]
  • [ 86864-60-0 ]
  • (2-(2-bromo-5-chlorophenoxy)ethoxy)(dimethyl)(2-methyl-2-propanyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.5% With potassium carbonate; potassium iodide; In 1-methyl-pyrrolidin-2-one; at 90℃; for 5h; To a solution of<strong>[13659-23-9]2-bromo-5-chlorophenol</strong> (50 g, 241 rnmol) in NJVIP (500mL) wa. added K?C03 (66.51 g, 482 mmol), (2-bromoethoxy)-tert-butyl-25 dimethylsilane (56 8 mL 265.1 mmol) and catalytic amount of KJ (800 mg, 4.80mmol), and the suspension was heated to 90 oc for 5 h. On completion, thesuspension vas cooled to room temperature and diluted vvith water (500 mL).Aqueous phase was extracted with ethyl acetate (3 x 250 mL). Combined organic layer was washed ·with water (500 mL), brine (500 mL) and dried over sodiumsulphate. Solvent was removed tmder reduced pressure to afford crude materialwhich v.·as purified by column chromatography (1 00-200 mesh size silica gel,eluting with a gradient of 100();6 hexanes to 5% ethyl acetate in hexanes) affording5 pure (2-(2-bromo-5-chlorophenoxy)ethoxy)(dimethyl)(2-methyl-2-propanyl)silane(72 g, 83.5%) as light yellov oiL Rr: 0.8 in 5() Ethyl acetate in hexane.
  • 10
  • [ 13659-23-9 ]
  • [ 86864-60-0 ]
  • diethyl 2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)malonate [ No CAS ]
  • 11
  • [ 86864-60-0 ]
  • [ 35344-95-7 ]
  • C12H22N2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In acetonitrile; at 80℃; for 2h; 2-bromoethoxy- xit y Id i met y I si I ane (CAS [86864-60-0]) (2.4 mL; 1 1 .4 mmol ) was added to a solution of 1 H-pyrazo le-4-carbaldehyde (CAS [35344-95-7] ) (910 mg; 9.5 mmol ) and K2CO3 ( 1 .6 g; 1 1 .4 mmol) in ACN (18 mL ). The reaction was heated at 80C for 2h. The reaction mixture was partitioned between a saturated solution of NaHCO; and EtOAc. The organic layer was separated, dried over MgS04, filtered and evaporated till dryness. The residue was purified by chromatography ov er silica gel ( Stationary phase: irregular SiOH 40 iim 120g, mobile phase gradient from: 100% DCM, 0% MeOH to 95% DCM, 5% MeOH). The fractions containing product were collected and ev aporated to dryness yielding 1 .6 g (65%) of intermediate 12 .
65% With potassium carbonate; In acetonitrile; for 2h;Reflux; A solution of 2-bromoethoxy-tert-butyldimethylsilane(CAS [86864-60-0]), (2.44mL;11.37mmol), <strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (CAS [35344-95-7]), (0.91g; 9.5mmol) and K2CO3 (1.57g; 11.37mmol) in ACN (18mL) was refluxed for 2 h. The mixture was cooled, poured into ice water and a saturated NaHCO3 solution, the aqueous layer was extracted with EtOAc. The organic layer was separated, dried over MgSO4, filtered and evaporated to dryness giving a crude compound which was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 120g, Mobile phase: Gradient from 100% DCM, 0% MeOH to 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 1.56g (yield 65%) of intermediate 18.
  • 12
  • [ 1184172-46-0 ]
  • [ 86864-60-0 ]
  • C13H21ClFNO2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 3h; Intermediate 35?? (620 mg, 4.20 mmol) was dissolved in DMF (12 mL), then (2-bromoethoxy)-tert-butyldimethylsilane (1.8 mL, 8.31 mmol) and K 2CO 3 (1.16 g, 8.39 mmol) were added and the mixture was stirred at 70 C for 3 h. Then the reaction was cooled to R.T., diluted with diethylether and washed with water and brine. The org. layer was dried over MgSO 4, filtered and concentrated. Flash column chromatography (80 g silica, Redisep, heptane/EtOAc, gradient 1:0 to 8:2) delivered intermediate 36?? as a yellowish oil (1.26 g, 98%).
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