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                            Chemical Structure| 100367-77-9
                            
                            Chemical Structure| 100367-77-9
                            
                            
    
                                Structure of 100367-77-9
                                
                            
    
                            
                        
    
    					
    
    						
    					
    
    				
    
    				
    
    					
    
    					
    
    					
    
    						
    
                                Chemical Structure| 100367-77-9
                            
    
    						
    
                                
                            
    
    					
    
    				
    
                    
                    
                    
    			
    
                
    
                    
                
    
                
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    CAS No.: 100367-77-9
    
                        
                        
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    Product Details of [ 100367-77-9 ]
     
        			
    
        				
        				
                            
        					
    CAS No. :100367-77-9
    
                            
                            
        					
    Formula :
                                
                                    C6H6BrNO2S
                                
                            
    
                            
                            
        					
    M.W : 
                                
                                    236.09  
                                
                            
    
                            
                            
        					
    SMILES Code : 
                                C1=C(C(OCC)=O)N=C(S1)Br
                            
    
                            
                            
                            
        					
    MDL No. :MFCD03788564
    
                            
                            
                            
        					
    InChI Key :CNHISCQPKKGDPO-UHFFFAOYSA-N
    
                            
                            
        					
    Pubchem ID :353965
    
                            
                            
        			
    
        			
        			
        			
    Safety of [ 100367-77-9 ]
    
        			
    
        				
        				
        					
                            
    GHS Pictogram:
                                
                                
                                    
                                
                                
                            
    
                            
                            
        					
    Signal Word:Warning
    
                            
                            
        					
    Hazard Statements:H315-H319-H335
    
                            
                            
                            
    Precautionary Statements:P261-P305+P351+P338
    
        					
                            
                            
                            
        				    
        			
    
        			
                    

        			
                    

        			
                    
        			
                    
        			
                    
        			
                    
        			
        			
    Computational Chemistry of [ 100367-77-9 ] Show Less
    
        			
    
                        
    
                            
    
                                
    Physicochemical Properties
    
                                
                                
    
                                    
                                    
                                        
    
                                            Num. heavy atoms 
                                            11
                                        
     
                                        
    
                                            Num. arom. heavy atoms 
                                            5
                                        
     
                                        
    
                                            Fraction Csp3 
                                            0.33
                                        
     
                                        
    
                                            Num. rotatable bonds 
                                            3
                                        
    
                                        
    
                                            Num. H-bond acceptors 
                                            3.0
                                        
    
                                        
    
                                            Num. H-bond donors 
                                            0.0
                                        
    
                                        
    
                                            Molar Refractivity 
                                            45.9
                                        
    
                                        
    
                                            TPSA ?
    Topological Polar Surface Area: Calculated from 
     Ertl P. et al. 2000 J. Med. Chem. 
    		
                                            67.43 ?2
                                        
    
                                        
                                
    
                            
    
                            
    
                                
    Lipophilicity
    
                                
    
                                    
                                    
                                        
    
                                            Log Po/w (iLOGP)?
    iLOGP: in-house physics-based method implemented from 
     Daina A et al. 2014 J. Chem. Inf. Model. 
    		
                                            2.22
                                        
    
                                        
    
                                            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 
    		
                                            2.53
                                        
    
                                        
    
                                            Log Po/w (WLOGP)?
    WLOGP: Atomistic method implemented from 
     Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model. 
    		
                                            2.08
                                        
    
                                        
    
                                            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. 
    		
                                            0.81
                                        
    
                                        
    
                                            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 
    		
                                            2.9
                                        
    
                                        
    
                                            Consensus Log Po/w?
    Consensus Log Po/w: Average of all five predictions 
    		
                                            2.11
                                        
    
                                        
                                
    
                            
    
                        
    
                        
    
                            
    
                                
    Water Solubility
    
                                
    
                                    
                                    
                                        
    
                                            Log S (ESOL):?
    ESOL: Topological method implemented from 
     Delaney JS. 2004 J. Chem. Inf. Model. 
    		
                                            -3.04
                                        
    
                                        
    
                                            Solubility
                                            0.217 mg/ml ; 0.00092 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. 
    		
                                            -3.59
                                        
    
                                        
    
                                            Solubility
                                            0.0603 mg/ml ; 0.000255 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 
    		
                                            -2.63
                                        
    
                                        
    
                                            Solubility
                                            0.547 mg/ml ; 0.00232 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. 
    		
                                            -5.94 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 
    		
                                            0.0 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)
    		
                                            2.86
                                        
    
                                        
                                
    
                            
    
                        
    
                    
    
                    
        			
        			
                    
                    
    
                        
    Application In Synthesis of [ 100367-77-9 ]
    
                        
    * 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 [ 100367-77-9 ]
      • 
                            
                            
                                
    • Downstream synthetic route of [ 100367-77-9 ]
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    [ 100367-77-9 ] Synthesis Path-Upstream   1~1
    
                            
                            
                                
    
                                    
                                    
                                        
      
                                            
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    • [ 100367-77-9 ]
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    • [ 5198-86-7 ]
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                                                    YieldReaction ConditionsOperation in experiment
                                                
    
                                                
                                            
                                                
                                                    
    
                                                        95%
                                                        With sodium tetrahydroborate; water; lithium chloride In tetrahydrofuran for 2 h; 
                                                        Preparation of (2-bromothiazol-4-yl)methanol (5)
    To a solution of ester 4 (10.0 g, 42.4 mmol, 1 equiv) in THF (200 mL) was added NaBH4 (4.81 g, 127 mmol, 3 equiv), LiCl (5.4 g, 130 mmol, 3 equiv) and H2O (40 mL). The resulting biphasic mixture was vigorously stirred for 2 h, after which TLC (20percent EtOAc:hexanes) showed complete consumption of starting material. The reaction was quenched with saturated aqueous NH4Cl (200 mL), diluted with EtOAc (200 mL), and the layers were separated. The aqueous layer was extracted with EtOAc (100 mL), and the organic layers were combined, dried (Na2SO4), filtered, and concentrated under reduced pressure to give the title compound as a yellow semi-solid (7.82 g, 95percent). Rf= 0.2 (SiO2, 20percent EtOAcrhexanes); 1H and 13C NMR of the product matched those previously reported (Wipf and Wang 2007).    		
                                                    
    
                                                
                                                    
    
                                                        91%
                                                         at 20 - 70℃;  for 8 h; 
                                                        2-Bromothiazol-4-Carboxylic acid ethyl ester (11.8g, 50.0mmol)Was dissolved in absolute ethanol (100 mL)Sodium borohydride (3.8 g, 100 mmol) was added, stirred at room temperature for 4 hours, and then heated to 70 ° C for 4 hours.The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1/5) to give a pale yellow oil (8.85 g, 91percent).
                                                    
    
                                                
                                                    
    
                                                        87%
                                                        With sodium tetrahydroborate In ethanol at 0 - 70℃;  for 7.5 h; 
                                                        At 0 , 2-bromo-thiazole-4-carboxylate (13.30g, 56.33mmol)In ethanol (150 mL) was added portionwiseSodium borohydride (4.263 g, 112.7 mmol),Stirring was continued at 0  0.5 hours.The mixture was stirred at room temperature for 3 hours,And heated to 70 ° C for 4 hours.The solvent was distilled off under reduced pressure,Slowly add water (100 mL)Extracted with ethyl acetate (100 mL x 3).Combine organic phase,Washed with saturated brine (50 mL)Dried over anhydrous sodium sulfate.Filtration, evaporation of the solvent under reduced pressure,The crude product was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 5/1)To give a colorless oil (9.5 g, 87percent).
                                                    
    
                                                
                                                
                                        
    
                                    
                                    
                                        
    
                                            
                                                
                                                
                                                
                                            
                                            
                                                
                                                    
    
                                                        87%
                                                        With sodium tetrahydroborate In ethanol at 0 - 20℃;  for 3 h; 
                                                        Into a 500-mL round-bottom flask, was placed ethyl 2-bromothiazole-4-carboxylate  (14 g, 59.30 mmol) and EtOH (200 mL). This was followed by the addition of  NaBH4 (2.3 g, 60.53 mmol) in portions at 0oC. The  resulting solution was stirred for 3 h at RT and then was quenched by the  addition of 100 mL of water. The resulting solution was extracted with 2x200 mL  of DCM and the organic layers combined and dried over anhydrous  Na2SO4, then concentrated under vacuum. This resulted in  10 g (87percent) of the title compound as colorless oil. MS-ESI: 195.9, 193.9 (M+1).
                                                    
    
                                                
                                                    
    
                                                        87%
                                                         at 0 - 20℃;  for 3 h; 
                                                        Into a 500-mL round-bottom flask was placed a solution of ethyl 2-bromothiazole-4-carboxylate(14 g, 59.3 mmol), EtOH (200 mL). This was followed by the addition of NaBH4(2.3 g, 60.5 mmol) in portions at 0°C. The resulting solution was stirred for 3 h at RT and then was quenched by the addition of 100 mL of water. The resulting solution was extracted with 2x200 mL of DCM.The organic layers were combined, dried over anhydrous Na2S04 and then concentrated under vacuum. This resulted in 10.0 g (87percent) of the title compound as colorless oil. MS-ESI: 195.9, 193.9(M+l).
                                                    
    
                                                
                                                    
    
                                                        81%
                                                         at 20℃;  for 3 h; Cooling
                                                        Into a 100-mL round-bottom flask was placed a solution of ethyl 2-bromo-1,3-thiazole-4- carboxylate (3 g, 12.71 mmol) in EtOH (30 mL). NaBH4 (1.0 g, 25.41 mmol) was added in portions with an ice/water bath. The resulting solution was stirred for 3 hr at room temperature. The reaction was then quenched by the addition of 100 mL of water in an ice/water bath. The resulting solution was extracted with 3x100 ml of ethyl acetate, and the combined organic layers were concentrated. This resulted in 2 g (81percent) of the title compound as yellow oil. MS-ESI: 196.2, 194.2 (M+1).
                                                    
    
                                                
                                                    
    
                                                        68%
                                                        With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; water at 0 - 20℃;  for 16 h; 
                                                        NaBH4 (2.49 g, 0.066 mol, 3 equiv), LiCl (2.79 g, 0.066 mol, 3 equiv) and H20 (30 mL) were added to a stirred solution ethyl 2-bromothiazole-4-carboxylate (1) (5.0 g, 0.022 mol, 1 equiv) in THF (50 mL) at 0 °C. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The reaction mixture was quenched with 1.5 M hydrochloric acid and the resulting mixture was extracted with ethyl acetate (2X150 mL). The combined organic layers were washed with water (150 mL), brine (150 mL), dried over Na2S04, filtered through celite bed and concentrated to provide compound 2 as a pale brown liquid (3.0 g, 68percent). LC-MS (ESI+): m/z 195.9 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): δ 7.48 (s, 1H), 5.43 (t, J = 5.7 Hz, 1H), 4.52 (d, J = 5.7 Hz, 2H).
                                                    
    
                                                
                                                    
    
                                                        67%
                                                        
    Stage #1: With lithium borohydride In tetrahydrofuran for 1 h; Cooling with an ice bath
    Stage #2: With methanol In tetrahydrofuran for 3.5 h;     		
                                                        Step 3 : (2-bromothiazol-4-yl)methanolA solution of ethyl 2-bromothiazole-4-carboxylate (7.821 g, 33.13 mmol) in THF (100 mL) was cooled in an ice-bath and treated portionwise with lithium borohydride (1.083 g, 49.70 mmol). After 1 hour MeOH (1.614 g, 2.040 mL, 50.36 mmol) was added over a period of half an hour. The reaction was allowed to stir for 3 hours and then the solvent was concentrated in vacuo and the resultant residue was dissolved in EtOAc, washed with HCl (2x), saturated sodium bicarbonate, followed by brine, dried (Na2SO4), concentrated and purified by column chromatography (EtOAc/Petroleum ether 1: 1) to give the required product as a colorless oil (4.3Og, 67percent Yield). 1H NMR (CDCl3, 400 MHz) δ 2.51 (IH, m), 4.75 (2H, m), 7.19 (IH, s); MS (ES+) 195.96
                                                    
    
                                                
                                                
                                        
    
                                        
    
                                    
                                    
                                        
    
                                            References:
                                            
                                                [1] Patent: WO2015/57585, 2015, A1, . Location in patent: Page/Page column 27; 28.
    
                                            
                                                [2] Patent: CN104478866, 2017, B, . Location in patent: Paragraph 0281; 0283; 0284.
    
                                            
                                                [3] Patent: CN104478869, 2017, B, . Location in patent: Paragraph 0142; 0143; 0144; 0145.
    
                                            
                                                [4] Patent: WO2017/184624, 2017, A1, . Location in patent: Page/Page column 185; 186.
    
                                            
                                                [5] Patent: WO2019/23147, 2019, A1, . Location in patent: Page/Page column 445.
    
                                            
                                                [6] Journal of Organic Chemistry, 2016, vol. 81, # 21, p. 10302 - 10320.
    
                                            
                                                [7] Patent: WO2019/23145, 2019, A1, . Location in patent: Page/Page column 393.
    
                                            
                                                [8] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 2766 - 2775[9] Zh. Obshch. Khim., 2017, vol. 87, # 12, p. 1947 - 1956,10.
    
                                            
                                                [10] Organic Letters, 2007, vol. 9, # 8, p. 1605 - 1607.
    
                                            
                                                [11] Patent: WO2018/200674, 2018, A1, . Location in patent: Page/Page column 72.
    
                                            
                                                [12] Patent: WO2010/129668, 2010, A1, . Location in patent: Page/Page column 48.
    
                                            
                                                [13] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1530 - 1533.
    
                                            
                                                [14] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5172 - 5177.
    
                                            
                                                [15] Organic Process Research and Development, 2017, vol. 21, # 10, p. 1602 - 1609.
    
                                            
                                        
    
                                    
                                
    
                            
                        
    
                        
                        
                        
                    
    
                    

        			
     
    
        		
    
        		
                
                
        		
                
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    Related Functional Groups of 
    [ 100367-77-9 ]
    
                        
                            
                                
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