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[ CAS No. 1246552-85-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1246552-85-1
Chemical Structure| 1246552-85-1
Chemical Structure| 1246552-85-1
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Product Details of [ 1246552-85-1 ]

CAS No. :1246552-85-1 MDL No. :MFCD28098506
Formula : C9H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LBKBAODKECLISV-UHFFFAOYSA-N
M.W : 240.05 Pubchem ID :122235386
Synonyms :

Calculated chemistry of [ 1246552-85-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.06
TPSA : 41.71 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) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 1.8
Log Po/w (SILICOS-IT) : 1.46
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0483 mg/ml ; 0.000201 mol/l
Class : Soluble
Log S (Ali) : -3.59
Solubility : 0.0614 mg/ml ; 0.000256 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.69
Solubility : 0.489 mg/ml ; 0.00204 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 1246552-85-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1246552-85-1 ]

* 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 [ 1246552-85-1 ]

[ 1246552-85-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1246552-85-1 ]
  • [ 123536-14-1 ]
  • [ 1620569-68-7 ]
YieldReaction ConditionsOperation in experiment
71.1% Stage #1: 5-bromoindolizine-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 10℃; for 0.333333h; Stage #2: (3R)-quinuclidin-3-amine dihydrochloride In dichloromethane at 0 - 20℃; for 3.16667h; 3 Synthesis of (R)-N-(quinuclidin-3-yl)indolizine-2-carboxamide (D1) General procedure: To a mixture of the aforementioned compound 20 (81mg, 0.5mmol), HATU (285mg, 0.75mmol) in dried CH2Cl2 was added DIPEA (387mg, 3.0mmol), and the solution was stirred at 0-10°C for 20min. Then (R)-3-aminoquinuclidine dihydrochloride (110mg, 0.55mmol) was slowly added with 10min. The mixture was stirred at room temperature for 3h. The solvent was removed and the residue was extracted with CH2Cl2/MeOH (20/1). The combined organic layer was concentrated and the residue was purified by silica gel column chromatography eluting with CH2Cl2/MeOH/ammonium hydroxide (100/10/1) to afford 96mg of compound D1 as light color oil. Yield: 74.3%.; 4.2.4.3 N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-bromoindolizine-2-carboxamide (D3) Yield 71.1%, oil. 1H NMR (400 MHz, DMSO-d6) δ 8.26 (d, J = 6.4 Hz, 1H), 8.18 (d, J = 1.3 Hz, 1H), 7.58 (d, J = 9.0 Hz, 1H), 7.08 (dd, J = 8.3, 1.3 Hz, 2H), 6.73 (dd, J = 9.0, 7.0 Hz, 1H), 4.08 (d, J = 6.5 Hz, 1H), 3.37-3.26 (m, 2H), 3.04 (ddd, J = 13.4, 7.8, 2.8 Hz, 1H), 2.96-2.79 (m, 4H), 2.02-1.83 (m, 2H), 1.70 (td, J = 7.9, 2.8 Hz, 2H), 1.47 (t, J = 11.7 Hz, 1H); 13C NMR (101 MHz,DMSO-d6) δ 163.3, 133.6, 124.1, 119.0, 118.5, 115.9, 114.2, 114.1, 101.6, 52.9, 46.5, 46.0, 45.9, 25.3, 24.2, 19.0; HRMS (ESI-TOF+) m/z Calcd. for C16H18BrN3O [M+1]+: 348.0706, found 348.0710.
71.1% 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 0 - 20℃; for 12h; 4 Add 5-bromoindolizine-2-carboxylic acid (120.0 mg, 0.5 mmol), 3- (3R) -aminoquinine dihydrochloride (109.5 mg, 0.6 mmol), DIPEA (0.53 mL, 3 mmol) to DMF (10mL), after cooling to 0 ° C, HATU (285.2mg, 0.75mmol) was slowly added, and the system was naturally heated to rt and reacted for 12h. The solvent was removed by rotary evaporation. Saturated brine (15 mL) was added to the reaction system, and extracted with DCM (15 mL x 3). The organic phase was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure after filtration. The residue was separated and purified through a silica gel column, and eluted with DCM / MeOH / aqueous ammonia = 90/10/1. 123.6 mg of the target compound was obtained as a transparent oil, and the yield was 71.1%.
  • 2
  • [ 1620569-94-9 ]
  • [ 1246552-85-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In tetrahydrofuran; methanol; water at 80℃; Reflux; The synthesis of indolizine-2-carboxylic acid (20) General procedure: To a solution of 19 dissolved in MeOH/THF/H2O (4/4/1) was added 20% of aqueous sodium hydroxide. The mixture was refluxed at 80°C overnight. The organic solvent was removed under the reduced pressure. The remained solution was cooled to 0-5°C and adjusted to pH 3-4 with 1M HCl. The suspension was stirred for 30min and filtered. The filter cake was dried to dryness to afford 0.16g (yield: 95.1%) of 20 which was used directly for the subsequent reaction.
  • 3
  • [ 1891813-55-0 ]
  • [ 1246552-85-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / acetic anhydride / 2 h / Reflux; Inert atmosphere 2: sodium hydroxide / tetrahydrofuran; methanol; water / 80 °C / Reflux
  • 4
  • [ 1620569-93-8 ]
  • [ 1246552-85-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1 h / 100 °C 2: acetic acid / acetic anhydride / 2 h / Reflux; Inert atmosphere 3: sodium hydroxide / tetrahydrofuran; methanol; water / 80 °C / Reflux
  • 5
  • [ 34160-40-2 ]
  • [ 1246552-85-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,4-diaza-bicyclo[2.2.2]octane / water; 1,4-dioxane / 3 h / 20 °C 2: 1 h / 100 °C 3: acetic acid / acetic anhydride / 2 h / Reflux; Inert atmosphere 4: sodium hydroxide / tetrahydrofuran; methanol; water / 80 °C / Reflux
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide In methanol for 10h; Reflux; 4 1d) 5-phenylindolizine-2-carboxylic acid General procedure: The compound obtained in 1c) (227.0 mg, 0.9 mmol) and NaOH (108.4 mg, 2.7 mmol) were added to MeOH (15 mL) and H 2 O (5 mL), and stirred under reflux for 10 h. Cooled to rt, and 1 M HCl (aq) was added. The pH was adjusted to 1. The precipitated solid was filtered and dried to obtain 205.0 mg of a pale yellow solid with a yield of 95.7%.
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