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[ CAS No. 1315366-78-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1315366-78-9
Chemical Structure| 1315366-78-9
Chemical Structure| 1315366-78-9
Structure of 1315366-78-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1315366-78-9 ]

CAS No. :1315366-78-9 MDL No. :MFCD19382315
Formula : C10H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XJAKYYQAYNQGRG-UHFFFAOYSA-N
M.W : 252.06 Pubchem ID :54594385
Synonyms :

Calculated chemistry of [ 1315366-78-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.4
TPSA : 50.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 2.04
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 2.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -3.38
Solubility : 0.104 mg/ml ; 0.000413 mol/l
Class : Soluble
Log S (Ali) : -3.11
Solubility : 0.197 mg/ml ; 0.000783 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.0295 mg/ml ; 0.000117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.29

Safety of [ 1315366-78-9 ]

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 [ 1315366-78-9 ]

* 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.

  • Downstream synthetic route of [ 1315366-78-9 ]

[ 1315366-78-9 ] Synthesis Path-Downstream   1~7

YieldReaction ConditionsOperation in experiment
With chromium(III) oxide; sulfuric acid
  • 2
  • [ 1315366-78-9 ]
  • [ 1315368-19-4 ]
YieldReaction ConditionsOperation in experiment
650 mg Stage #1: 3-bromoquinoline-8-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 60℃; for 16h; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h; Intermediate Bl: Synthesis of 3-bromo-quinoline-8-carboxylic acid amide Intermediate Bl: Synthesis of 3-bromo-quinoline-8-carboxylic acid amide 3-Bromo-quinoline-8-carboxylic acid (900 mg, 3.6 mmol) is dissolved in DMF (27 mL) and CDI (1.3 g, 7.9 mmol) is added. The mixture is heated at 60 °C for 16 hr before it is cooled down to room temperature. Then 28% ammonium hydroxide aqueous solution (4.5 g, 36 mmol) is added and the mixture is stirred for another 1 hr. The saturated NaHC03 aqueous solution (30 mL) is added along with water (30 mL). A white solid is formed and it is filtered, rinsed with more water and dried to give 650 mg of the title product.
  • 3
  • [ 1187056-55-8 ]
  • [ 1315366-78-9 ]
  • [ 2092997-05-0 ]
YieldReaction ConditionsOperation in experiment
83% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; tert-butyl [(1S,3R,5S)-3-(3-[(3-bromoquinolin-8-yl)carbonyl]amino}pyridin-4-yl)-5-methylcyclohexyl]carbamate To a solution of fert-butyl (l S,3R,5S)-3-(3-aminopyridin-4-yl)-5- methylcyclohexylcarbamate (200 mg, 0.65 mmol) and 3-bromoquinoline-8-carboxylic acid (200 mg, 0.79 mmol) in NN-dimethylformamide (5 mL) were added Ν,Ν- diisopropylethylamine (240 μ^, 1.35 mmol) and N,N,N' N'-tetramethyl-0-(7-azabenzotriazol- l-yl)uronium hexafluorophosphate (390 mg, 1.05 mmol). After the reaction mixture was stirred at r.t. for 2 hours, it was quenched by the addition of water. The precipitate was collected by filtration and washed with water twice. Then it was redissolved in ethyl acetate to give a solution which was washed with brine and dried over sodium sulfate. After the solvent was evaporated, the crude product was purified by Biotage Isolera (flash purification system with hexane/ethyl acetate at a ratio from 0 to 100%) to give the desired compound (290 mg, 83%). LCMS calculated for C27H32BrN403 (M+H)+ m/z = 539.2; found 539.1.
  • 4
  • [ 2415204-35-0 ]
  • [ 1315366-78-9 ]
  • [ 2415201-14-6 ]
  • [ 2415201-15-7 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; 2.30 Method 30: Preparation of Compounds 56 and 57: 3-(4-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-8-carboxylic acid and 3-(4-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-8-carboxylic acid 3-(4-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-8-carboxylic acid and 3-(4-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-8-carboxylic acid A mixture of ((R)-tetrahydrofuran-2-yl)(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-6-azaspiro[2.5]octan-6-yl)methanone (680 mg, 1.65 mmol) and 3-bromoquinoline-8-carboxylic acid (500 mg, 1.98 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (117 mg, 0.17 mmol) and potassium phosphate (702 mg, 3.31 mmol) in dioxane (10 mL) and water (2 mL) was stirred for 2 h at 80 °C under nitrogen atmosphere. The resulting mixture was extracted with EtOAc (2 x 20mL). The mixture was cooled to room temperature and concentrated. The crude product was purified by Prep-HPLC with water (0.1% FA) and ACN (40% up to 55% in 20 min). The product was separated by Chiral HPLC with the following conditions: Column: CHIRALPAK IG, 20×250mm, 5 µm; mobile phase: MTBE (0.1% FA) and EtOH (hold 50% EtOH in 30 min); Detector: UV254 nm to afford the first eluting peak as Compound 56 (66 mg, 7%) and the second eluting peak as Compound 57 (61.9 mg, 7%) as a white solid. Compound 56: 1H -NMR (CD3OD, 400 MHz) δ (ppm): 9.39 (s, 1H), 8.86 (s, 1H), 7.70 (d, J= 6.8 Hz, 1H), 7.38 (d, J= 7.6 Hz, 1H), 7.92-7.73 (m, 3H), 7.48 (d, J= 8.0 Hz, 2H), 4.82-4.61 (m, 1H), 4.02-3.68 (m, 4H), 3.60-3.48 (m, 1H), 3.47-3.40 (m, 1H), 2.35-2.11 (m, 2H), 2.10-1.85(m, 3H), 1.79-1.55 (m, 2H), 1.43-1.25 (m, 2H), 1.24-1.10 (m, 1H), 1.05-0.91 (m, 1H). LCMS (ES, m/z): 457 [M+H]+. Compound 57: 1H -NMR (CD3OD, 400 MHz) δ (ppm): 9.38 (s, 1H), 8.85 (s, 1H), 7.69 (d, J= 7.2 Hz, 1H), 7.37 (d, J= 7.2 Hz, 1H), 7.97-7.69 (m, 3H), 7.47 (s, 2H), 4.82-4.64 (m, 1H), 4.05-3.61 (m, 4H), 3.60-3.38 (m, 2H), 2.32-1.81 (m, 5H), 1.79-1.57 (m, 2H), 1.52-1.12 (m, 3H), 1.09-0.91 (m, 1H). LCMS (ES, m/z): 457 [M+H]+.
  • 5
  • [ 1315366-78-9 ]
  • [ 2868276-61-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 2 h / 20 °C 1.2: 4 h / 20 °C 2.1: caesium carbonate; palladium diacetate; BINAP / toluene / 18 h / 80 °C / Inert atmosphere
  • 6
  • [ 1315366-78-9 ]
  • [ 2868276-41-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 2 h / 20 °C 1.2: 4 h / 20 °C 2.1: caesium carbonate; palladium diacetate; BINAP / toluene / 18 h / 80 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane; methanol / 4 h / 0 - 25 °C
  • 7
  • [ 74-89-5 ]
  • [ 1315366-78-9 ]
  • [ 2868276-62-2 ]
YieldReaction ConditionsOperation in experiment
59 % Stage #1: 3-bromoquinoline-8-carboxylic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; Stage #2: methylamine In dichloromethane at 20℃; 3-bromo-N-methylquinoline-8-carboxamide (44): 43 (1 g, 3.97 mmol) was dissolved in dichloromethane, added di(1H-pyrrol-1-yl)methanone, stirred for 2h at room temperature until gas release was completed, added aqueous methylamine solution (4 mL,40%), and stirred at room temperature for 4h. After the reaction was completed, the reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 44 (620 mg, 59%)
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