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[ CAS No. 1093966-37-0 ] {[proInfo.proName]}

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Chemical Structure| 1093966-37-0
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Product Details of [ 1093966-37-0 ]

CAS No. :1093966-37-0 MDL No. :MFCD22024490
Formula : C8H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :IIDGMDQWRBRUKM-UHFFFAOYSA-N
M.W : 211.06 Pubchem ID :58540815
Synonyms :

Calculated chemistry of [ 1093966-37-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.23
TPSA : 49.81 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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 2.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.142 mg/ml ; 0.000674 mol/l
Class : Soluble
Log S (Ali) : -3.26
Solubility : 0.115 mg/ml ; 0.000544 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.0898 mg/ml ; 0.000426 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 1093966-37-0 ]

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

Application In Synthesis of [ 1093966-37-0 ]

* 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 [ 1093966-37-0 ]

[ 1093966-37-0 ] Synthesis Path-Downstream   1~15

  • 1
  • 2-amino-5-bromo-3-methyl-benzamide [ No CAS ]
  • [ 1093966-37-0 ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: 2-amino-5-bromo-3-methyl-benzamide With triethylamine; trifluoroacetic anhydride In tetrahydrofuran for 3h; Cooling with ice; Stage #2: With potassium carbonate In methanol; water at 70℃; 147 To a tetrahydrofuran solution (10 mL) of 2-amino-5-bromo- 3-methylbenzamide (580 mg) and triethylamine (1.6 mL) was added dropwise trifluoroacetic acid anhydride (0.91 mL) under ice- cooling, and the mixture was stirred for 3 hr. Water was added, and the mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in methanol (5 mL) , water (5 mL) and potassium carbonate (700 mg) were added, and the mixture was stirred overnight at 700C. Methanol was evaporated under reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to NH-silica gel column chromatography (eluate: ethyl acetate), and the obtained crude crystal was recrystallized (diisopropyl ether-hexane) to give the title compound (240 mg, yield 45%) as colorless crystals. MS:213(MH++1) .
  • 2
  • [ 507-40-4 ]
  • [ 1093966-37-0 ]
  • 2,2'-(diazene-1,2-diyl)bis(5-bromo-3-methylbenzonitrile) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium iodide In acetonitrile at -10℃; Inert atmosphere; 1.2; 2.2; 3.2; 4.2 2) Synthesis of 2,2'-(diazepine-1,2-diyl)bis(5-bromo-3-methylbenzonitrile) 2-Amino-5-bromo-3-methylbenzonitrile (7.5 g, 35.55 mmol), KI (7.6 g, 45.6 mmol) was dissolved in dry acetonitrile (120 mL) t-BuOCl (5.9 g, 54.7 mmol) was added dropwise.The addition time is 30-45 min, and the reaction is kept overnight.After the reaction is completed, it is raised to room temperature.1M sodium thiosulfate (100 mL) was quenched.Dichloromethane (100*3) liquid extraction,Dry over anhydrous magnesium sulfate, concentrate under reduced pressure, and recover solvent.Recrystallized from dichloromethane,That is, the product 2,2'-(diazene-1,2-diyl)bis(5-bromo-3-methylbenzonitrile),It is a reddish brown solid (11.6 g, 80%).
  • 3
  • [ 69797-49-5 ]
  • [ 1093966-37-0 ]
YieldReaction ConditionsOperation in experiment
83.1% With hydrogen bromide; In water; dimethyl sulfoxide; ethyl acetate; at 80℃; Dissolve <strong>[69797-49-5]2-amino-3-methylbenzonitrile</strong> (10.0g, 75.6mmol) and DMSO (7mL) in ethyl acetate (140mL), and dropwise add HBr aqueous solution (3mL) at room temperature for 30-60min. After the dropwise addition is completed, the reaction bottle is closed at 50-80 C, and the reaction time is 1-6h. After the reaction was completed, 1M potassium carbonate aqueous solution (150 mL) was added for washing, and dichloromethane (120 * 3) was used for liquid separation, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.The target product, 2-amino-5-bromo-3-methylbenzonitrile, was obtained as a yellow solid (13.3 g, 83.1%).
82% With hydrogen bromide; In water; dimethyl sulfoxide; ethyl acetate; at 50 - 80℃; <strong>[69797-49-5]2-Amino-3-methylbenzonitril</strong>e (8.0 g, 60.5 mmol) in EtOAc (5 mL)HBr aqueous solution (2 mL) was added dropwise at room temperature.The dropping time is 15-45min,After the addition is completed,The reaction flask is at 50-80 C,Closed reaction,The reaction time is 1-6 h.After the reaction is completed,Wash with 1M aqueous potassium carbonate solution (100 mL).Dichloromethane (100*3),Dried over anhydrous magnesium sulfate,Concentrated under reduced pressure,The target product 2-amino-5-bromo-3-methylbenzonitrile is obtained.It was a yellow solid (10.5 g, 82%).
  • 4
  • [ 1093966-37-0 ]
  • C16H12Br2N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tert-butylhypochlorite; potassium iodide / acetonitrile / -10 °C / Inert atmosphere 2: boron trifluoride diethyl etherate / dichloromethane / 115 - 130 °C 3: toluene-4-sulfonic acid / toluene / 105 - 120 °C
  • 5
  • [ 1093966-37-0 ]
  • 2,2'-(diazene-1,2-diyl)bis(5-bromo-3-methylbenzonitrile) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.1% With tert-butylhypochlorite; potassium iodide In acetonitrile at -10℃; Inert atmosphere; 1.2; 2.2; 3.2; 4.2 2) Synthesis of 2,2 '-(diazene-1,2-diyl) bis (5-bromo-3-methylbenzonitrile) Add 2-amino-5-bromo-3-methylbenzonitrile (9.0 g, 42.7 mmol),KI (9.1g, 54.7mmol) was dissolved in dry inert gas-protected acetonitrile (150mL) at -10 ° C.T-BuOCl (7.2g, 65.6mmol) was added dropwise for 30-45min,Incubate the reaction overnight, and then warm to room temperature after the reaction.1M sodium thiosulfate (100mL) was quenched, and dichloromethane (150 * 3) was separated and extracted.Dry over anhydrous magnesium sulfate, concentrate under reduced pressure, recover the solvent, recrystallize with dichloromethane,The product 2,2 '-(diazene-1,2-diyl)bis (5-bromo-3-methylbenzonitrile) is obtained,As a red-brown solid (14.3 g, 82.1%).
  • 6
  • [ 1093966-37-0 ]
  • 5-bromo-2-(5-bromo-3-((3,3-dimethylbut-2-ylidene)amino)-7-methyl-2H-indazol-2-yl)-3-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tert-butylhypochlorite; potassium iodide / acetonitrile / -10 °C / Inert atmosphere 2: boron trifluoride diethyl etherate / dichloromethane / 115 - 130 °C
  • 7
  • [ 1093966-37-0 ]
  • 6-bromo-4,8-dimethylquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 17 h / -10 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: ammonium acetate / 3 h / 110 °C
  • 8
  • [ 1093966-37-0 ]
  • 4,8-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 17 h / -10 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: ammonium acetate / 3 h / 110 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere
  • 9
  • [ 1093966-37-0 ]
  • 5-(4,8-dimethylquinazolin-6-yl)-4-(furan-2-yl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 17 h / -10 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: ammonium acetate / 3 h / 110 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 3 h / 90 °C / Inert atmosphere
  • 10
  • [ 1093966-37-0 ]
  • 5-(4,8-dimethylquinazolin-6-yl)-4-(4-fluorophenyl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 17 h / -10 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: ammonium acetate / 3 h / 110 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 80 °C / Inert atmosphere 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere
  • 11
  • [ 1093966-37-0 ]
  • [ 75-16-1 ]
  • 1-(2-amino-5-bromo-3-methylphenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.59% Stage #1: 2-amino-5-bromo-3-methylbenzonitrile; methylmagnesium bromide In tetrahydrofuran at -10 - 20℃; for 17h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; for 1h; 2.1 First step1- (2-amino-5-bromo-3-methylphenyl) ethan-1-one 2b Under an argon atmosphere, 2-amino-5-bromo-3-methylbenzonitrile 2a (2 g, 9.4761 mmol, prepared by a known method "WO2008156757") was dissolved in 100 mLIn tetrahydrofuran,Methyl magnesium bromide (2 M, 23.69 mL) was added dropwise at -10 ° C. The reaction was stirred at room temperature for 17 hours, 10% hydrochloric acid was added, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted three times with ethyl acetate (100 mL x 3) and combined. The organic phase was washed once with sodium chloride solution (80 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified with a CombiFlash rapid preparation device with eluent system B to obtain the title product 2b (1.85 g, yield: 85.59% ).
  • 12
  • [ 583-75-5 ]
  • [ 1093966-37-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide; toluene-4-sulfonic acid / acetonitrile / 20 °C 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
  • 13
  • [ 922170-67-0 ]
  • [ 557-21-1 ]
  • [ 1093966-37-0 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; Inert atmosphere; N-(5-bromo-2-chloro-3-cyanophenyl)methanesulfonamide (A15) General procedure: A mixture of intermediate A14 (4.50 g, 10.96 mmol), Zn(CN)2 (644 mg,5.48 mmol) and Pd(PPh3)4 (633 mg, 0.55 mmol) in anhydrous DMF (30 mL) was heated at 80 °C overnight under N2. After cooling to room temperature, the reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified via silica gel chromatography (PE/EA = 3/1) to afford intermediate A15 (1.76 g, 52 %) as a white solid.
  • 14
  • [ 1093966-37-0 ]
  • 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 80 °C / Inert atmosphere 2: acetic acid; sodium nitrite / water / 20 °C
  • 15
  • [ 1093966-37-0 ]
  • [ 73183-34-3 ]
  • 2-amino-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere; 3-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (A7) To a solution of 5-Amino-3-bromobenzonitrile (5.00 g, 25.38 mmol), Bis(pinacolato)diboron (7.73 g, 30.45 mmol), Pd(dppf)Cl2·CH2Cl2 (1.05 g, 1.27 mmol), and AcOK (7.47 g, 76.13 mol) in anhydrous DMSO (50 mL) was heated at 80 °C overnight under N2. The mixture was partitioned between EtOAc and H2O, The combined organics were collected then washed with brine and dried over anhydrous Na2SO4. The crude material was purified on silica gel column (DCM/MeOH = 200/1) to afford intermediate A7 (4.83 g, 78 %) as a yellow solid.
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