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[ CAS No. 1344046-13-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1344046-13-4
Chemical Structure| 1344046-13-4
Chemical Structure| 1344046-13-4
Structure of 1344046-13-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1344046-13-4 ]

CAS No. :1344046-13-4 MDL No. :MFCD20327982
Formula : C10H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VHZHOJLAAXVYSL-UHFFFAOYSA-N
M.W : 252.06 Pubchem ID :71819690
Synonyms :

Calculated chemistry of [ 1344046-13-4 ]      Expand+

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) : 1.73
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 : 2.27

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 : 1.33

Safety of [ 1344046-13-4 ]

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 [ 1344046-13-4 ]

* 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 [ 1344046-13-4 ]

[ 1344046-13-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 1344046-13-4 ]
  • [ 2253094-62-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 60 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water; ethanol / 80 °C
  • 2
  • [ 1344046-13-4 ]
  • [ 2253084-03-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 60 °C 2.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 110 °C
  • 3
  • [ 1448427-99-3 ]
  • 3-bromoquinoline-7-carboxylic acid [ No CAS ]
  • C20H17BrN6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% Stage #1: 3-bromoquinoline-7-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 6-[4-(propan-2-yl)-4H-1,2,4-triazol-3-yl]pyridin-2-amine In N,N-dimethyl-formamide at 60℃; 36 Example 36 HBTU (451 mg, 1.2 mmol, 1.2 eq) was added to a solution of 3-bromoquinoline-7- carboxylic acid (250 mg, 1.0 mmol, 1.0 eq) and Hunig’s base (0.87 mL, 5.0 mmol, 5.0 eq) in DMF (3.0 mL) and the reaction was stirred for 10 min at room temperature.6-(4-Isopropyl- 4H-1,2,4-triazol-3-yl)pyridin-2-amine (1-6) (222 mg, 1.1 mmol, 1.1 eq) was added and the resultant suspension was heated at 60 °C overnight. The reaction was partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with sat. NaHCO3, 10% citric acid, and brine. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The resultant brown gum was purified by column chromatography eluting with DCM/MeOH (0% MeOH , 8% MeOH) to afford pure compound 36 (82 mg, 0.19 mmol, 19%) as a brown amorphous solid: LCMS (ESI) m/z 437.06 (M+1).
  • 4
  • [ 1344046-13-4 ]
  • [ 2415204-35-0 ]
  • [ 2415201-78-2 ]
  • [ 2415201-79-3 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; 2.35 Method 35: Preparation of Compounds 120 and 121: 3-(4-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid and 3-(4-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid. 3-(4-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid and 3-(4-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid A solution 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 (450 mg, 1.10 mmol), 3-bromoquinoline-7-carboxylic acid (689 mg, 2.74 mmol), [1,1'-Bis(di phenylphosphino)ferrocene]dichloropalladium (89.3 mg, 0.11 mmol) and potassium phosphate (702 mg, 3.31 mmol) in 1,4-dioxane (15 mL) and water (3 mL) was stirred for 2 h at 80 °C under a nitrogen atmosphere. The mixture was cooled to room temperature and concentrated under reduced pressure. The crude product was purified by Prep-HPLC with water (0.1% FA) and ACN (40.0% up to 60.0% in 10 min). The product was separated by Chiral HPLC with the following conditions: Column: CHIRALPAK IF, 0.46 × 5 cm, 3 µm; mobile phase: hexanes (containing 0.1% formic acid): dichloromethane (3:1) and Methanol (hold 50% Methanol in 15 min); Detector: UV 254 nm to afford the first eluting peak as Compound 120 (119.2 mg, 24%) as a yellow solid and the second eluting peak as Compound 121 (119.3 mg , 34%) as a white solid. Compound 120: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 13.30 (br, 1H), 9.39-9.38 (m, 1H), 8.74 (s, 1H), 8.60 (s, 1H), 8.15-8.08 (m, 2H), 7.86 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 4.72-4.55 (m, 1H), 3.78-3.59 (m, 6H), 2.15-2.10 (m, 1H), 2.04-1.73 (m, 4H), 1.68-1.42 (m, 2H), 1.28-0.88 (m, 4H). LCMS (ES, m/z): 457 [M+H]+. Compound 121: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 13.33 (br, 1H), 9.39 (s, 1H), 8.76 (s, 1H), 8.60 (s, 1H), 8.17-8.09 (m, 2H), 7.87 (d, J=8.0 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 4.70-4.58 (m, 1H), 3.78-3.61 (m, 4H), 3.27-3.18 (m, 2H), 2.16-1.71 (m, 5H), 1.68-1.47 (m, 2H), 1.28-0.90 (m, 4H). LCMS (ES, m/z): 457 [M+H]+.
  • 5
  • [ 1344046-13-4 ]
  • [ 571150-08-8 ]
  • [ 2550442-79-8 ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 3-bromoquinoline-7-carboxylic acid With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 0.25h; Stage #2: N,N-diethyl 3-amino-6-chlorobenzenesulfonamide In ethyl acetate at 0 - 20℃; for 16h; Inert atmosphere; 1; II General Experimental Procedure II General procedure: T3P (35.0 equiv., 50% solution in EtOAc) was added to a stirred solution of the corresponding acid (1.0 equiv.) in pyridine (0.8 M) at 0 °C, and the reaction mixture was stirred for 15 minutes. Then, the corresponding aniline (1.0 equiv.) was added at 0 °C, and the reaction mixture was left to stir at rt for additional 16 hours under Nitrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography and LC/MS. Upon completion of the reaction, the reaction mixture was filtered through a neutral alumina pad twice to remove the excess of T3P. The filtrate was concentrated in vacuo and the crude product was purified by prep- HPLC. After purification, the fractions containing the desired product were concentrated to a minimal volume, filtered through 0.4 ^m syringe filter and lyophilized to afford the product in > 95% purity.
  • 6
  • [ 1344046-13-4 ]
  • [ 2550436-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: caesium carbonate; copper(l) iodide; N,N-dimethylglycine hydrochoride / 1,4-dioxane / 16 h / 90 °C / Sealed tube
  • 7
  • [ 1344046-13-4 ]
  • [ 2550438-37-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 110 °C / Inert atmosphere; Sealed tube
  • 8
  • [ 1344046-13-4 ]
  • [ 106877-33-2 ]
  • [ 2550438-32-7 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; 1; I General Experimental Procedure I General procedure: Corresponding carboxylic acid (1.0 equiv) and corresponding aniline (1.1 equiv) were suspended in dry N,N-dimethyl formamide under argon atmosphere followed by the addition of triethylamine (1.2 equiv). Then HATU (1-[bis(dimethylamino) methylene]-1H-1,2,3- triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (228 mg, 0.6 mmol, 1.2 equiv) was added, and the reaction mixture was stirred for 16 hours at rt. After dilution with water, the mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). The fractions containing the desired product were combined and treated with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the desired product in >95% purity as determined by HPLC.
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