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Chemical Structure| 5437-45-6 Chemical Structure| 5437-45-6

Structure of 5437-45-6

Chemical Structure| 5437-45-6

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CAS No.: 5437-45-6

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Product Details of [ 5437-45-6 ]

CAS No. :5437-45-6
Formula : C9H9BrO2
M.W : 229.07
SMILES Code : O=C(OCC1=CC=CC=C1)CBr
MDL No. :MFCD00000190
InChI Key :JHVLLYQQQYIWKX-UHFFFAOYSA-N
Pubchem ID :62576

Safety of [ 5437-45-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:3265
Packing Group:Ⅲ

Computational Chemistry of [ 5437-45-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 50.18
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.3 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.27
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.75
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.97
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.43
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.57
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.4

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.1
Solubility 0.182 mg/ml ; 0.000797 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.96
Solubility 0.253 mg/ml ; 0.0011 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.75
Solubility 0.0403 mg/ml ; 0.000176 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.74 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.7

Application In Synthesis of [ 5437-45-6 ]

* 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 [ 5437-45-6 ]

[ 5437-45-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 35661-51-9 ]
  • [ 5437-45-6 ]
  • [<i>N</i>'-(9<i>H</i>-fluoren-9-ylmethoxycarbonyl)-hydrazino]-acetic acid benzyl ester [ No CAS ]
  • 2
  • [ 309947-86-2 ]
  • [ 5437-45-6 ]
  • [ 1108637-35-9 ]
  • 3
  • [ 22876-16-0 ]
  • [ 5437-45-6 ]
  • [ 910322-62-2 ]
YieldReaction ConditionsOperation in experiment
57% To a portion of <strong>[22876-16-0]6-methyl-3H-benzooxazol-2-one</strong> (450 mg, 3.02 mmol) in DMF (10 mL) at 23 C. was added K2CO3 (900 mg, 6.51 mmol), and the reaction mixture was stirred for 30 min. Benzyl-2-bromoacetate (909 μL, 5.74 mmol) was slowly added to the reaction mixture, while stirring. After 17 h, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with 1.0 N HCl (100 mL), saturate aqueous NaHCO3 (100 mL), then brine (100 mL), and then was dried (Na2SO4) and concentrated to yield the crude product that was purified by silica gel column chromatography (20-50% EtOAc in hexanes) to afford (6-methyl-2-oxobenzooxazol-3-yl)acetic acid benzyl ester (512 mg, 57%).
  • 4
  • [ 129799-08-2 ]
  • [ 5437-45-6 ]
  • C20H28N2O6 [ No CAS ]
  • 5
  • [ 79950-42-8 ]
  • [ 5437-45-6 ]
  • [ 1351472-15-5 ]
YieldReaction ConditionsOperation in experiment
88.7% With potassium carbonate; In acetone; at 40℃; Example 4.; Preparation 2-Ally-3 -(carbomethoxy)benzyloxybenzaldehyde; Reaction Scheme: Experimental:Preparation of 2-Allyl-3-benzyloxybenzaldehyde (3)Table 7.Experimental ProcedureTo a solution of <strong>[79950-42-8]2-allyl-3-hydroxybenzaldehyde</strong> (1) (1.00 g, 0.006 mol) in acetone (20 mL) was added powdered potassium carbonate (3.30 g) and benzyl bromoacetate (2) (1.53 g, 0.006 mol). The reaction mixture was stirred at 40 °C (oil bath temperature) for 5 h. The reaction mixture was checked by tic (Note 1). The reaction was complete. The mixture was filtered, and the filtrate was concentrated in vacuo to get crude viscous liquid. The crude product was purified by silica gel column chromatography using a mixture of ethyl acetate and hexanes (4- 10percent) to get colorless viscous liquid (1.73 g, 88.7percent). 1H NMR (CDC13, 300 Hz) 3.89 (m, 2H), 4.74 (s, 2H), 4.95 - 5.00 (m, 2H), 5.22 (s, 2H), 5.97-6.06 (m, 1H), 6.97 (m, 1H), 7.29-7.34 9m, 6H), 7.54 (m, 1H). Note 1 : Completion of the reaction was monitored by thin layer chromatography (TLC) thin layer silica gel plate; eluent: 10percent ethyl acetate in hexanes.
  • 6
  • [ 138007-24-6 ]
  • [ 5437-45-6 ]
  • [ 1354805-15-4 ]
YieldReaction ConditionsOperation in experiment
3.4 g With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 4h; To a suspension (39 mL) of <strong>[138007-24-6]ter<strong>[138007-24-6]t-butyl piperidine-4-carboxylate</strong></strong> (2.6 g) in acetonitrile was added diisopropylethylamine (4.4 mL), subsequently, benzyl bromoacetate (2.0 mL) was added at room temperature in portions, and the mixture was stirred for 4 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. This was washed with an aqueous saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3?0:1) to obtain the title compound (3.4 g) having the following physical property values.; TLC: Rf 0.66 (hexane:ethyl acetate=2:1); 1H-NMR (CDCl3): delta 1.44 (s, 9H) 1.68-1.92 (m, 4H) 2.10-2.35 (m, 3H) 2.83-2.96 (m, 2H) 3.26 (s, 2H) 5.16 (s, 2H) 7.25-7.41 (m, 5H).
  • 7
  • [ 50-00-0 ]
  • [ 230301-11-8 ]
  • [ 5437-45-6 ]
  • [ 1449369-14-5 ]
  • [ 1449369-15-6 ]
YieldReaction ConditionsOperation in experiment
111 mg; 45 mg Step 209.2: To a solution of 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert- butyl ester (279mg) in MeCN (10ml) was added Cs2CO3 (407mg) followed by benzyl bromoacetate (0.2ml). The resulting white suspension was stirred at RT for 48h, diluted with EA and washed with water and brine. The aq. phases were extracted with EA. The combined org. layers were dried (MgS04), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 25g cartridge, DCM/MeOH 97/3 for 10CV) to afford 371 mg of oil. The oil was purified by preparative chiral HPLC (I) to afford the two regioisomers, both as mixture of benzyl and ethyl ester that formed during the evaporation of the fractions after HPLC purification: Step 209.3: The Boc protecting group of 1-benzyloxycarbonylmethyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester was cleaved using a method analogous to that of Example 16 step 16.4 to give (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester. Step 209.4: To a solution of (4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (176mg) in MeOH was added formaldehyde (36.5% in water, 0.052ml_) followed by NaBH3CN (29mg) and AcOH (0.5ml_). The reaction mixture was stirred at RT overnight. DCM was added and the mixture was washed with sat. NaHCO3. The aq. layer was extracted with DCM, the combined org. layers were dried (MgS04), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 10g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in %B: 25 for 3CV, 25 to 50 over 2CV, 50 for 5CV, 50 to 100 over 3CV, 100 for 2CV) to afford (5-methyl-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-1-yl)-acetic acid benzyl ester (39mg, yellow oil). (5-Methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-2-yl)-acetic acid benzyl ester (1 1 1 mg, colourless oil). LC-MS (B): tR = 0.54min; [M+H]+: 286.16. 1H-NMR (CDCl3): 7.40-7.33 (m, 5H); 7.18 (s, 1 H); 5.21 (s, 2H); 4.89 (s, 2H); 3.50 (s, 2H); 2.86 (t, 2H, 6.0Hz); 2.76 (t, 2H, 5.5Hz); 2.49 (s, 3H). Roesy signal seen between CH2 at 4.89ppm and CH at 7.18ppm. (5-Methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1 -yl)-acetic acid benzyl ester (45mg, pale yellow solid). LC-MS (B): tR = 0.54min; [M+H]+: 286.16. 1H-NMR (CDCl3): 7.40-7.33 (m, 6H); 5.21 (s, 2H); 4.85 (s, 2H); 3.47 (s, 2H); 2.75 (t, 2H, 6.0Hz); 2.67 (t, 2H, 5.5Hz); 2.49 (s, 3H). Roesy signal seen between CH2 at 4.85ppm and CH2 at 2.67ppm. Step 215.2: The final compound was prepared using a method analogous to that of Example 14 step 14.2, (5-methyl-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-2-yl)-acetic acid benzyl ester replacing intermediate 14.1 and using MeOH instead of MeOH/AcOH. LC-MS (B): tR = 0.17min; [M+H]+: 196.29.
  • 8
  • [ 102831-44-7 ]
  • [ 5437-45-6 ]
  • [ 1239129-44-2 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 4h; 10138] A suspension of diethyl 2-t-butyloxycarbonylami- nomalonate (5.0 g), potassium carbonate (3.0 g), and benzyl 2-bromoacetate (5.4 g) in DMF (20 mL) was stirred at 50for 4 hours. The reaction mixture was cooled, and then poured into diluted hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, and then purification was performed with n-hexaneethyl acetate (5:1), to obtain the title compound (6.5 g, yield: 85%) as colorless oil.10139] ‘H NMR (CDC13) ? (ppm): 7.32 (5H, m), 6.1 (1H, s), 5.11 (2H, s), 4.21 (4H, m), 3.53 (2H, s), 1.41 (9H, s), 1.22 (6H, t, J=7.i Hz)10140] MS (FAR): mlz 424 (M+H)
  • 9
  • [ 42726-73-8 ]
  • [ 5437-45-6 ]
  • 4-benzyl 1-tert-butyl 2-methoxycarbonylsuccinate [ No CAS ]
  • 10
  • [ 42726-73-8 ]
  • [ 5437-45-6 ]
  • 4-benzyl 1-tert-butyl 2-benzoyloxy-2-methoxycarbonylsuccinate [ No CAS ]
  • 4-benzyl 1-tert-butyl 2-benzoyloxy-2-methoxycarbonylsuccinate [ No CAS ]
  • 11
  • [ 5918-93-4 ]
  • [ 5437-45-6 ]
  • dibenzyl 2,2'-(2-oxo-1H-imidazole-1,3(2H)-diyl)diacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
240 mg With caesium carbonate; In acetone; at 65℃; for 6h;Sealed tube; Step 1. A mixture of lH-imidazol-2(3H)-one (100 mg, 1.19 mmol), cesium carbonate (853 mg, 2.62 mmol) and benzyl 2-bromoacetate (0.40 mL, 2.50 mmol) in acetone (10 mL) was sealed and heated in an oil bath at 65 °C for 6 h. The reaction mixture was filtered and concentrated in vacuo. The residual solid was purified by FCC (80 g silica gel, eluted with gradient 30percent~100percent EtOAc-hexanes) to afford dibenzyl 2,2'-(2-oxo-lH-imidazole- l,3(2H)-diyl)diacetate (240 mg) as a colorless oil. LC-MS retention time = 1.16 min; m/z = 381.3 [M+H]+. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7^m-particles; Solvent A = 100percent Water/ 0.05percent TFA; Solvent B = 100percent Acetonitrile/0.05percent TFA; Flow Rate = 0.8 mL/min. Start percent B = 2; Final percent B = 98; Gradient Time = 1.5 minutes; Wavelength = 220 nm). NMR (400 MHZ, CDCh) delta ppm 7.46 - 7.32 (m, 10H), 6.33 (s, 2H), 5.22 (s, 4H), 4.48 (s, 4H).
  • 12
  • [ 33543-78-1 ]
  • [ 5437-45-6 ]
  • ethyl 1-[2-(benzyloxy)-2-oxoethyl]-1H-imidazole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% To a solution ethyl lH-imidazole-2-carboxylate (6 g, 42.8 mmol , prepared as per the procedure depicted in Synthetic communication, 44(7), 968-975, 2014) in DMF (30 ml) at 25-30 °C followed by potassium carbonate (7.1 g, 51.3 mmol) under stirring. After 15 minutes of stirring benzyl bromoacetate (9.8 g, 42.8 mmol) was added drop-wise at same temperature. The progress of reaction was monitored by TLC (methanol: DCM, 1:9). After complete consumption of starting material the reaction mixture was filtered through celite bed to remove insoluble inorganic and poured on to water (150 ml). The aqueous reaction mixture was extracted with dichloro methane (3x 60 ml). The organic extracts were combined and washed with brine (60 ml), dried over anhydrous sodium sulphate. The volatiles were removed under reduced pressure to yield 12 g of yielded ethyl l-[2-(benzyloxy)-2-oxoethyl]-lH-imidazole-2-carboxylate in 97percent yield.
 

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