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CAS No. : | 169044-96-6 | MDL No. : | MFCD21868787 |
Formula : | C9H10BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SFXCMXLNSVHKCE-UHFFFAOYSA-N |
M.W : | 260.08 | Pubchem ID : | 19701951 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 56.32 |
TPSA : | 61.55 Ų |
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) : | -6.25 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 2.31 |
Log Po/w (WLOGP) : | 1.83 |
Log Po/w (MLOGP) : | 1.77 |
Log Po/w (SILICOS-IT) : | 1.69 |
Consensus Log Po/w : | 1.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.03 |
Solubility : | 0.244 mg/ml ; 0.00094 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.24 |
Solubility : | 0.149 mg/ml ; 0.000574 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.1 |
Solubility : | 0.208 mg/ml ; 0.000798 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.76 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312-P330 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.06% | With bromine; In dichloromethane; at 20℃; for 20h; | To a solution of compound 34 (4.0 g, 0.02 mol) in DCM(200 mL) was added bromine (1.36 mL, 0.02 mol). Themixture was stirred at room temperature for 20 h. It wasdiluted with saturated sodium hydrogen sulfite (50 mL) andthe aqueous solution was extracted with DCM. The combinedorganic layers were washed with brine, dried overNa2SO4 and filtered. The residue was purified by silica gelcolumn chromatography eluting with PE/EA to give whitepowder 35 (4.71 g, 82.06%). 35: 1H NMR delta (400 MHz,CDCl3) 8.04 (s, 1H), 6.14 (s, 1H), 5.87 (s, 2H), 3.89 (s, 3H),3.87 (s, 3H). |
With bromine; In chloroform; at 0 - 20℃; | A-8a (15.0 g, 82.8 mmol, LO equiv.) is dissolved in chloroform (750 mL) and cooled to 0 C. A solution of bromine (4.2 mL, 82.8 mmol, 1.0 equiv.) in chloroform (10 mL) is added dropwise and the reaction mixture stirred for 1 h at rt. Then the reaction mixture is quenched with sodium thiosulphate (aqu.) and extracted with EtOAc. The combined organic layer is washed with saturated NaHC03 solution, dried over Na2S04 and concentrated in vacuo. The crude product is washed with hexane to give the final compound A-9b (HPLC method: GVK_LCMS_05: tret [min] = 1 .76; [M+H]+ = 260.0). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With ammonium formate; at 165℃; for 18.0h; | A solution of <strong>[169044-96-6]methyl 2-amino-5-bromo-4-methoxybenzoate</strong> (75 mg, 0.29 mmol) and ammonium formate (38 mg, 0.8 mmol) in formamide (1 mL) was heated at 165 C for 18h. The mixture was allowed to cool to room temperature then diluted with an excess of water. The solid formed was collected by filtration and washed with water then ethyl acetate and dried to give 6-bromo-7-methoxyquinazolin-4(3H)-one (53 mg, 72% yield) as a pale yellow solid. MS (EI) for C9H7BrN2O2: 255, 257 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | at 165℃; for 18.0h; | Reagent Preparation 1; [00451] STEP I : A solution of methyl 2-amino-5-bromo-4- mcthoxybenx.oaie (75 nig. 0.29 mmol) and ammonium formate (38 mg, 0.8 mmol ) in formamide ( I inL) was heated at 165 "C for 18li. The mixture was allowed to cool to room temperature then dilulcd with an excess of waler. The solid formed was collected by filtration aiul washed with water then cihyl acctaic and dried to give 6-broirK>-7-mcthox yquinazolin- (3/-A)-onc (53 mg, 72% yield) as a pale yellow sol id. MS (EI) for 255, 257 ( IT1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.5 g | With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.0h; | Step 2: Methyl 2-amino-5-bromo-4-methoxybenzoateTo a stirred suspension of <strong>[169045-04-9]2-amino-5-bromo-4-methoxybenzoic acid</strong> (6.3 g, 0.025 mol) and potassium carbonate (7.06 g, 0.051 mol) in N,ll-dimethyl formamide (63 mL) was added methyl iodide (5.45 g, 0.038 mol) dropwise at 0C. After the addition was complete, the reaction mixture was stirred at room temperature for 1 h. The mixture was poured into ice cold water (500 mL) and extracted with ethyl acetate (2 x 200 mL). The combined organic layers were washed with water (100 mL) followed by brine solution, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using column chromatography (100-200 mesh silica gel, 20% EtOAc in hexane) to afford the title compound as white solid (5.5 g, 83% yield). *H NMR (400 MHz, DMSO-d6) : delta 7.78 (s, 1H), 6.85 (brs, 2H), 6.44 (s, 1H), 3.80 (s, 3H), 3.75 (s, 3H). ESI-MS: Calculated mass: 258.98; Observed mass: 258.3 [M-H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In water; acetic acid; at 20 - 50℃; for 24.0h; | Step 3: 6-Bromo-7-methoxyquinazoiine-2,4( lH,3H)-dioneTo a stirred suspension of <strong>[169044-96-6]methyl 2-amino-5-bromo-4-methoxybenzoate</strong> (5.5 g, 0.021 mol) in acetic acid (25 mL) was added 0.1 M aqueous solution of potassium cyanate (7.49 g, 0.10 mol) dropwise at room temperature. The reaction mixture was stirred at 50C for 24 h. The solid separated was filtered, washed with water (20 mL) followed by 10% EtOAc in hexane (50 mL) and dried under vacuum to afford the corresponding urea.To the stirred suspension of the above urea in methanol (20 mL) was added 2N sodium hydroxide (10 mL). The reaction mixture was stirred at 90C for 1 h. The mixture was cooled to room temperature, acidified with 3M hydrochloric acid to pH 3. The solid obtained was filtered and dried under vacuum to afford the title compound as white solid (3.5 g, 61% yield). *H NMR (400 MHz, DMSO-d6) : delta 11.29 (s, 1H), 11.18 (S, 1H), 7.94 (S, 1H), 6.74 (s, 1H), 3.90 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In N,N-dimethyl-formamide; at 70℃; for 24.0h; | To a solution of compound 35 (500 mg, 1.92 mmol) inDMF (10 mL) were added 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane (452 mg,2.31 mmol), Pd(dppf)2Cl2 (140 mg, 0.19 mmol) andCs2CO3 (1253 mg, 3.85 mmol). The mixture was stirred at70 C for 24 h with the protection of N2. It was cooled to RTand diluted with water and extracted with ethyl acetate. Thecombined organic layers were washed with brine. It wasdried over Na2SO4 and filtered. The filtrate was concentratedand the residue was purified by silica gel columnchromatography eluting with cyclohexane/EA (uv254,20:1) to give pale-yellow powder 36 (198.0 mg, 43.0%). 36:1H NMR (500 MHz, CDCl3) delta 7.63 (s, 1H), 7.35 (dd, J =8.6, 4.2 Hz, 4H), 6.94 (dd, J = 24.0, 8.6Hz, 4H), 6.07 (s,1H), 5.26 (t, J = 7.3 Hz, 1H), 4.99 (s, 2H), 4.64 (dd, J =13.8, 3.5 Hz, 1H), 4.41 (s, 1H), 3.81 (s, 3H), 3.80 (s, 3H),3.19 (d, J = 7.3 Hz, 2H), 2.78 (dd, J = 16.1, 13.9 Hz, 1H),2.65 (dd, J = 16.2, 2.7 Hz, 1H), 1.72 (s, 3H), 1.69 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid; at 100℃; for 16.0h;Sealed tube; | A-9b (12.0 g, 46.1 mmol, 1.0 equiv.) is dissolved in acetonitrile (120 mL) and treated with methane sulfonic acid (24 mL). The reaction mixture is heated in a sealed tube to 100 C for 16 h. The acetonitrile is evaporated, water and sat. NaOH solution is added to the reaction mixture and the precipitate filtered off to give the desired product A-10a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 100℃; for 12.0h; | 1 19. Methyl 4-amino-6-methoxy[1,1 '-biphenyl]-3-carboxylate was prepared using the process described in synthetic procedure A from phenylboronic acid and substituting methyl 2-amino-5-bromo-4- methoxybenzoate for methyl bromoanthranilate. |
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