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[ CAS No. 1183031-46-0 ] {[proInfo.proName]}

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Chemical Structure| 1183031-46-0
Chemical Structure| 1183031-46-0
Structure of 1183031-46-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1183031-46-0 ]

CAS No. :1183031-46-0 MDL No. :MFCD12874244
Formula : C12H14BrNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KGGVXTYYRWMJCI-UHFFFAOYSA-N
M.W : 316.15 Pubchem ID :47003416
Synonyms :

Calculated chemistry of [ 1183031-46-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 71.35
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.26
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 2.64
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 2.67

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.77
Solubility : 0.0536 mg/ml ; 0.00017 mol/l
Class : Soluble
Log S (Ali) : -4.52
Solubility : 0.0095 mg/ml ; 0.00003 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.56
Solubility : 0.0879 mg/ml ; 0.000278 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.49

Safety of [ 1183031-46-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1183031-46-0 ]

* 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 [ 1183031-46-0 ]

[ 1183031-46-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 24424-99-5 ]
  • [ 20776-50-5 ]
  • [ 1183031-46-0 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine; In N,N-dimethyl-formamide; at 50℃; Step 1 : To a 250-mL round bottom flask was added <strong>[20776-50-5]2-amino-4-bromo-benzoic acid</strong> (2.5 g, 11.6 mmol) and anhydrous dimethyl formamide (45 mL). Triethylamine (4.8 mL, 34.7 mmol) was subsequently added followed by the di-tert-butyl dicarbonate (3.8 g, 17.4 mmol). The reaction mixture was stirred heated at 50 C overnight. The reaction mixture was cooled to room temperature and poured into a flask containing water (150 mL). The resulting mixture was washed with ethyl acetate (2 x 10 mL). The aqueous phase was acidified to a pH range of 4-5 with 10% v/v aqueous HCl solution. The acidified mixture was extracted with dichloromethane (3 x 50 mL). The combined organic phase was washed with brine (15mL), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to give 4-bromo-2-tert-butoxycarbonylamino-benzoic acid (3.4 g; 94%) as beige solid.
56% With triethylamine; In N,N-dimethyl-formamide; at 50℃; for 16h; To a solution of <strong>[20776-50-5]2-<strong>[20776-50-5]amino-4-bromobenzoic acid</strong></strong> (30.0 g, 139 mmol) and triethylamine (58.0 ml, 420 mmol) in N,N-dimethylformamide (300 ml) was added di-tert-butyl dicarbonate (48.0 ml, 210 mmol). After stirring at 50 C for 16 hours, the mixutre was diluted with water, adjusted to pH'H NMR (400MHz, DMSO-d6) delta [ppm] = 10.59 (s, 1H), 8.52 (d, 1H), 7.88 (d, 1H), 7.28 (dd, 1H), 1.46 (s, 9H)
56% With triethylamine; In N,N-dimethyl-formamide; at 50℃; for 16h; To a solution of <strong>[20776-50-5]2-<strong>[20776-50-5]amino-4-bromobenzoic acid</strong></strong> (30.0 g, 139 mmol) and triethylamine (58.0 ml, 420 mmol) in N,N-dimethylformamide (300 ml) was added di-tert-butyl dicarbonate (48.0 ml, 210 mmol).After stirring at 50 C for 16 hours, the mixutre was diluted with water, adjusted to pH<5 with 0.5M hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, concentrated and purified by colunm chromatography on silica gel (1000 mesh, petroleum ether: ethyl acetate = 2:1 to 1:3) to give the title compound (26.0 g, 95% purity, 56% yield) as white solid.?H NMR (400MHz, DMSO-d6) [ppm] = 10.59 (s, 1H), 8.52 (d, 1H), 7.88 (d, 1H), 7.28 (dd, 1H), 1.46 (s, 9H)
50% With sodium hydroxide; In 1,4-dioxane; at 20℃; General procedure: The aminobenzoic acid was dissolved in dioxane followed byaddition of 1 M NaOH aq di-tert-butyl dicarbonate was dissolvedin dioxane and the resulting solution was added, dropwise, to thereaction mixture, which was allowed to stir at room temperature.The progress of the reaction was analysed by analytical LC/MS andfound to be slow. After 24 h extra di-tert-butyl dicarbonate wasadded in order to complete the reaction. After another 24-48 hstirring the reaction was worked up. After evaporation of parts ofthe solvent, 0.1 M NaOH aq was added and the reaction mixturewas washed with ether. The product precipitated from the alkalinewater phase by dropwise addition of 1 M HCl to pH around 6. Thedifference of pKa-values of the product and the starting materialwas used to obtain good separation.
With dmap; triethylamine; In acetonitrile; at 20℃; for 2h; General procedure: To a solution of anthranilic acid (0.5g, 3.64mmol) in acetonitrile (10mL) were added TEA (0.73g, 7.28mmol), Boc anhydride (0.95g, 4.37mmol), and DMAP (0.044g, 0.36mmol). The mixture was stirred at rt for 2.0 h. CMPI (1.1g, 4.36mmol) was added in one lot to the reaction mixture. The reaction mixture was stirred at rt for 10 min. 1N HCl (20mL) was added to the reaction and the mixture was extracted two times with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was crystallized in DCM and MeOH to afford 0.56g (95%) of 1H-benzo[d][1,3]oxazine-2,4-dione as an off white solid. 1H NMR (400MHz, DMSO) delta 7.14-7.16 (d, J=8Hz, 1H), 7.23-7.27 (t, J=16Hz,1H), 7.72-7.74 (t, J=8Hz, 1H), 7.90-7.92 (d, J=8Hz,1H), 11.72 (s, 1H). 13C NMR (100MHz, DMSO-d6) delta 110.6, 115.7, 123.9, 129.3, 137.3, 141.8, 147.5, 160.3. IR (thin film) 3461, 3173, 2937, 1984, 1753, 1604, 1486, 1358, 1258, 1138, 1009, 765, 673, 492. ES-MS (m/z): 161.8 (M+-H). MP (C): 236.

  • 2
  • [ 830-43-3 ]
  • [ 1183031-46-0 ]
  • tert-butyl(5-bromo-2-(((4-(trifluoromethyl)phenyl)sulfonyl)carbamoyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% General procedure: All solid chemicals used were dried in vacuum over P2O5 overnight.The acid derivative and CDI were dissolved in dry THF underN2 atmosphere and the mixture was allowed to stir at 66-68 C for2 h. The sulfonamide and DBU dissolved in THF were added to thereaction mixture and stirring was continued at room temperature(4 h-overnight). Method B2: The solvent was removed in vacuo. The crude materialwas dissolved in EtOAc or DCM (25 ml), washed with 5% citricacid aq (2 15 ml) and brine (15 ml), dried with MgSO4, filteredand evaporated in vacuo. Purification by silica column chromatog-NNNOClN OHNHNNHNOSHONHOHOONHOHN+HNNH2NH2NN ONOClO NNHHNNHNOSHONHOHONHOHN+HNNH2NH2HHHHANN ONOClNONHNNHNOSHONHOHONHOHN+HNNH2H NH2HBHCR155C159 A157R155C159 A157R155C159 A157O RORR = OH, OMe, or NSO2ArROFigure 5. A schematic 2D illustration of the three poses (A-C) considered. Hydrogen bond interactions to the backbone of bE2 (R155, A157, and C159) are shown by dashedlines. For pose C the hydrophobic pocket is depicted by a solid line.raphy gave the product as a DBU salt. The material was washedwith 0.1 N NaHSO4 aq to give the pure product.
  • 3
  • [ 1183031-46-0 ]
  • 4-(methoxymethyl)-3-nitroaniline [ No CAS ]
  • [ 128625-52-5 ]
  • tert-butyl (5-bromo-2-[4-(methoxymethyl)-3-nitrophenyl]carbamoyl}phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; To a solution of 4-bromo-2-((tert-butoxycarbonyl)amino)benzoic acid (22.6 g, 90% purity 64.2 mmol), 4-(methoxymethyl)-3-nitroaniline (6.50 g, 90% purity, 32.1 mmol) and benzotriazol-l-yl- oxytripyrrolidinophosphonium hexafluorophosphate (33.4 g, 64.2 mmol) in N,N-dimethylformamide (80 ml) was added N,N-diisopropylethylamine (17.0 ml, 96.0 mmol), the mixture was stirred at room temperature for 16 hours. Another batch was prepared under similar reaction conditions (2.00 g of 4- (methoxymethyl)-3-nitroaniline, 90% purity).The two mixtures were combined, diluted with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (1000 mesh, petroleum ether: ethyl acetate = 20: 1 to 5: 1) to give the title compound (11.6 g, 90% purity) as a light yellow solid. NMR (400MHz, DMSO-d6) delta [ppm] = 10.84 (s, 1H), 9.98 (s, 1H), 8.50 (d, 1H), 8.28 (d, 1H), 8.01 (dd, 1H), 7.78 (d, 1H), 7.70 (d, 1H), 7.40 (dd, 1H), 4.72 (s, 2H), 3.35 (s, 3H), 1.44 (s, 9H)
  • 4
  • [ 1183031-46-0 ]
  • [ 76561-16-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of anthranilic acid (0.5g, 3.64mmol) in acetonitrile (10mL) were added TEA (0.73g, 7.28mmol), Boc anhydride (0.95g, 4.37mmol), and DMAP (0.044g, 0.36mmol). The mixture was stirred at rt for 2.0 h. CMPI (1.1g, 4.36mmol) was added in one lot to the reaction mixture. The reaction mixture was stirred at rt for 10 min. 1N HCl (20mL) was added to the reaction and the mixture was extracted two times with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was crystallized in DCM and MeOH to afford 0.56g (95%) of 1H-benzo[d][1,3]oxazine-2,4-dione as an off white solid. 1H NMR (400MHz, DMSO) delta 7.14-7.16 (d, J=8Hz, 1H), 7.23-7.27 (t, J=16Hz,1H), 7.72-7.74 (t, J=8Hz, 1H), 7.90-7.92 (d, J=8Hz,1H), 11.72 (s, 1H). 13C NMR (100MHz, DMSO-d6) delta 110.6, 115.7, 123.9, 129.3, 137.3, 141.8, 147.5, 160.3. IR (thin film) 3461, 3173, 2937, 1984, 1753, 1604, 1486, 1358, 1258, 1138, 1009, 765, 673, 492. ES-MS (m/z): 161.8 (M+-H). MP (C): 236.
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