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[ CAS No. 125096-72-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 125096-72-2
Chemical Structure| 125096-72-2
Chemical Structure| 125096-72-2
Structure of 125096-72-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 125096-72-2 ]

CAS No. :125096-72-2 MDL No. :MFCD09738589
Formula : C8H4BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NVMDCMMESVPNHN-UHFFFAOYSA-N
M.W :243.49 Pubchem ID :14397530
Synonyms :

Calculated chemistry of [ 125096-72-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.25
TPSA : 25.78 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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 3.19
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 2.58
Log Po/w (SILICOS-IT) : 3.25
Consensus Log Po/w : 2.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0257 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.0963 mg/ml ; 0.000396 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.8
Solubility : 0.00384 mg/ml ; 0.0000158 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 125096-72-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 125096-72-2 ]

* 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 [ 125096-72-2 ]

[ 125096-72-2 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 6318-37-2 ]
  • [ 125096-72-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
50% In pyridine for 4h; Heating;
  • 2
  • [ 125096-72-2 ]
  • [ 1784763-10-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
55% In pyridine for 4h; Heating;
  • 3
  • [ 125096-72-2 ]
  • [ 2360559-78-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
65% In pyridine for 4h; Heating;
  • 4
  • [ 125096-72-2 ]
  • [ 1055978-68-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
70% In pyridine for 4h; Heating;
  • 5
  • [ 98-16-8 ]
  • [ 125096-72-2 ]
  • [ 2361545-72-2 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol at 20℃;
  • 6
  • [ 20776-51-6 ]
  • [ 125096-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Reflux 2: trichlorophosphate / Reflux
Multi-step reaction with 2 steps 1: 6 h / 150 °C 2: thionyl chloride / N,N-dimethyl-formamide / 25 h / 80 °C
Multi-step reaction with 2 steps 1: 6 h / 150 °C 2: thionyl chloride / N,N-dimethyl-formamide / 25 h / 80 °C
  • 7
  • [ 77150-35-7 ]
  • [ 125096-72-2 ]
YieldReaction ConditionsOperation in experiment
97.6% With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 25h; Preparation of intermediate i-2 Weigh intermediate i-1 (18 g, 0.080 mol) and place it in a 250 mL eggplant-shaped bottle, add 100 mL thionyl chloride and 1 drop of anhydrous DMF. Reflux at 80 °C for 25 h. TLC monitors the end of the reaction. After the reaction, the mixture was allowed to stand to cool to room temperature, and concentrated in vacuo to remove the solvent.Add dichloromethane to the reaction flask to the fully dissolved state, then slowly pour the product-dissolved dichloromethane solution into ice water, stir for 5 minutes, and separate the organic phase. The organic phase was washed with saturated sodium bicarbonate aqueous solution until the aqueous layer was neutral, the separated organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain 19.01 g of yellow solid, with a yield of 97.6%.
With trichlorophosphate Reflux;
  • 8
  • [ 125096-72-2 ]
  • [ 2361520-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: isopropyl alcohol / 20 °C 2: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
  • 9
  • [ 125096-72-2 ]
  • [ 57260-71-6 ]
  • [ 2368909-93-5 ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine In butan-1-ol at 90℃; for 6h; 1 Step 1 A mixture of 8-bromo-4-chloroquinazoline (119) (2 g, 8 mmol), tert-butyl piperazine-1-carboxylate (1.7 g, 90 mmol) and DIPEA (2.0 g, 16 mmol) in 25 mL BuOH was heated at 90° C. for 6 hours. The solvent was removed under reduced pressure and the crude product was purified by silica gel flash chromatography, which was eluted with 0-30% EtOAc/petroleum ether and gave tert-butyl 4-(8-bromoquinazoline-4-yl)piperazine-1-carboxylate (120) as a white solid (3.0 g, 90% yield). 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.07 (d, J=7.5 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), 3.80-3.72 (m, 4H), 3.68-3.62 (m, 4H), 1.50 (s, 9H). LCMS (ESI) m/z 393, 395 (M+H).
  • 10
  • [ 125096-72-2 ]
  • [ 2368909-94-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 90 °C 2: potassium carbonate; palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere
  • 11
  • [ 125096-72-2 ]
  • [ 2368909-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 90 °C 2.1: potassium carbonate; palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere 3.1: ozone / methanol; dichloromethane / 0.5 h / -50 °C 3.2: 1.33 h / 20 °C / Inert atmosphere
  • 12
  • [ 125096-72-2 ]
  • [ 2368909-96-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 90 °C 2.1: potassium carbonate; palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere 3.1: ozone / methanol; dichloromethane / 0.5 h / -50 °C 3.2: 1.33 h / 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.67 h / -80 °C 4.2: 3 h / -80 °C
  • 13
  • [ 125096-72-2 ]
  • [ 2368909-97-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 90 °C 2.1: potassium carbonate; palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere 3.1: ozone / methanol; dichloromethane / 0.5 h / -50 °C 3.2: 1.33 h / 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.67 h / -80 °C 4.2: 3 h / -80 °C 5.1: pyridine / 5 h / 80 °C
  • 14
  • [ 125096-72-2 ]
  • [ 2368909-98-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 6 h / 90 °C 2.1: potassium carbonate; palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere 3.1: ozone / methanol; dichloromethane / 0.5 h / -50 °C 3.2: 1.33 h / 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran / 0.67 h / -80 °C 4.2: 3 h / -80 °C 5.1: pyridine / 5 h / 80 °C 6.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 5 h
  • 15
  • [ 125096-72-2 ]
  • [ 2667680-05-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: potassium carbonate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere 4.1: acetic acid / dichloromethane / 1 h / Reflux 4.2: 0.5 h
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 16
  • [ 125096-72-2 ]
  • [ 2667680-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: potassium carbonate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere 4.1: acetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 1 h / 80 °C
  • 17
  • [ 125096-72-2 ]
  • [ 2667680-14-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: potassium carbonate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere 4.1: acetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere
  • 18
  • [ 125096-72-2 ]
  • [ 2667680-41-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 1 h / 80 °C 2.1: potassium carbonate / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 2.2: 18 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere
  • 19
  • [ 125096-72-2 ]
  • [ 2667679-98-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 1 h / 80 °C 2.1: potassium carbonate / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere 2.2: 18 h / 80 °C / Inert atmosphere 3.1: acetic acid; methanol / 20 °C 3.2: 0.5 h / 20 °C
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 20
  • [ 125096-72-2 ]
  • [ 2667680-44-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
  • 21
  • [ 125096-72-2 ]
  • [ 2667680-43-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: potassium carbonate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere
  • 22
  • [ 125096-72-2 ]
  • [ 2667680-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
  • 23
  • [ 125096-72-2 ]
  • [ 2667680-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: caesium carbonate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere
  • 24
  • [ 125096-72-2 ]
  • [ 2667680-48-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: potassium carbonate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere
  • 25
  • [ 125096-72-2 ]
  • [ 2667680-49-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: potassium phosphate / 1,4-dioxane; water / 0.5 h / Inert atmosphere 3.2: 1 h / 100 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: XPhos Pd G2; potassium phosphate tribasic / water; tetrahydrofuran / 6 h / 70 °C / Inert atmosphere
  • 26
  • [ 22080-96-2 ]
  • [ 125096-72-2 ]
  • [ 2667680-40-0 ]
YieldReaction ConditionsOperation in experiment
95.2% With potassium carbonate In acetonitrile at 80℃; for 1h; Preparation of intermediate i-3 Intermediate i-2 (14g, 0.057mol), 4-hydroxy-2,6-dimethoxybenzaldehyde (11g, 0.060mol) and potassium carbonate (23.8g, 0.171mol) were added to a 250mL reaction flask, 100mL of acetonitrile was added and stirred at 80 °C and refluxed for 1h. During the reaction, a solid precipitated out.TLC detects the end of the reaction. After the reaction, it was cooled to room temperature, filtered with suction, washed with water, and dried to obtain 21.3 g of yellow solid, with a yield of 95.2%.
95% With potassium carbonate In acetonitrile at 80℃; for 1h; 4.1.3 Synthesis of intermediate i-3 A mixture of i-2 (14g, 0.057mol), 4-hydroxy-2,6-dimethoxybenzaldehyde (11g, 0.06mol) and potassium carbonate (23.8g, 0.171mol) in 100mL acetonitrile was heated at 80°C for 1h. TLC monitored completion of the reaction. Reaction mixture was cooled to room temperature and filtered. The filtrated cake was poured into 100mL water and stirred for 30min. The precipitate was filtered to obtain a yellow solid as intermediate i-3 (21.3g, 95.2%). 1H NMR (400MHz, CDCl3) δ 10.48 (s, 1H), 8.95 (s, 1H), 8.35 (dd, J=8.0, 1.2Hz, 1H), 8.26 (dd, J=8.0, 1.2Hz, 1H), 7.57 (t, J=8.0Hz, 1H), 6.53 (s, 2H), 3.91 (s, 6H).
  • 27
  • [ 131088-02-3 ]
  • [ 125096-72-2 ]
  • [ 2667680-45-5 ]
YieldReaction ConditionsOperation in experiment
78.4% With sodium hydrogencarbonate; potassium iodide In acetonitrile at 60℃; for 60h; Preparation of intermediate i-6 Weigh 5-chloro-2,4-dihydroxybenzaldehyde (10g, 0.058mol), intermediate i-2 (15.52g, 0.064mol), sodium bicarbonate (6.33g, 0.075mol), potassium iodide (4.81g, 0.029 mol) was placed in a 500 mL eggplant-shaped bottle, 200 mL acetonitrile was added, and the temperature was raised to 60 °C to react for 60 hours, and the end of the reaction was monitored by TLC. After the reaction, the mixture was allowed to stand to cool to room temperature, and a light yellow solid was obtained by suction filtration. The crude product was stirred with water for 30 minutes and then suction filtered to obtain 17.25 g of a light yellow solid. The yield was 78.4%.
78.4% With sodium hydrogencarbonate; potassium iodide In acetonitrile at 60℃; for 60h; 4.1.6 Synthesis of intermediate i-6 A mixture of i-2 (15.52g, 0.064mol), 2,4-dihydroxy-5-chlorobenzaldehyde (10.00g, 0.058mol), sodium bicarbonate (6.33g, 0.075mol) and potassium iodide (0.48g, 0.003mol) in 200mL acetonitrile was heated at 60°C for 60h. TLC monitored completion of the reaction. Reaction mixture was cooled to room temperature and filtered. The filtrated cake was poured into 100mL water and stirred for 30min. The precipitate was filtered to obtain a light yellow solid as intermediate i-6 (17.25g, 78.4%). 1H NMR (400MHz, DMSO-d6) δ 11.42 (s, 1H), 10.27 (s, 1H), 8.90 (s, 1H), 8.47-8.42 (m, 2H), 7.84 (s, 1H), 7.75 (t, J=7.9Hz, 1H), 7.20 (s, 1H).
  • 28
  • [ 125096-72-2 ]
  • [ 2667680-04-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 29
  • [ 125096-72-2 ]
  • [ 2762793-97-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 30
  • [ 125096-72-2 ]
  • [ 2762793-98-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 31
  • [ 125096-72-2 ]
  • [ 2667680-42-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere
  • 32
  • [ 125096-72-2 ]
  • [ 2762793-93-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 33
  • [ 125096-72-2 ]
  • [ 2667680-06-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 34
  • [ 125096-72-2 ]
  • [ 2667680-07-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 35
  • [ 125096-72-2 ]
  • [ 2667680-08-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 36
  • [ 125096-72-2 ]
  • [ 2667680-10-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 1 h / 80 °C
  • 37
  • [ 125096-72-2 ]
  • [ 2667680-00-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 38
  • [ 125096-72-2 ]
  • [ 2667680-11-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 1 h / 80 °C
  • 39
  • [ 125096-72-2 ]
  • [ 2667680-16-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 40
  • [ 125096-72-2 ]
  • [ 2667680-17-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 41
  • [ 125096-72-2 ]
  • [ 2667680-18-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 42
  • [ 125096-72-2 ]
  • [ 2667680-19-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 43
  • [ 125096-72-2 ]
  • [ 2667680-20-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 44
  • [ 125096-72-2 ]
  • [ 2667680-21-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 45
  • [ 125096-72-2 ]
  • [ 2667680-22-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 46
  • [ 125096-72-2 ]
  • [ 2667680-23-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 60 h / 60 °C 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 4: acetic acid / dichloromethane / 1 h / 40 °C
  • 47
  • [ 125096-72-2 ]
  • [ 2667680-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 80 °C 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride; acetic acid / methanol / 0.5 h / 20 °C
  • 48
  • [ 77150-35-7 ]
  • [ 125096-72-2 ]
YieldReaction ConditionsOperation in experiment
97% With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 25h; 4.1.2 Synthesis of intermediate i-2 A mixture of i-1 (18g, 0.08mol), thionyl chloride (100mL) and one drop of DMF was heated at 80°C for 25h. TLC monitored completion of the reaction. Reaction mixture was cooled to room temperature and evaporated to give a residue, which was dissolved in dichloromethane and washed with water and sodium bicarbonate aqueous solution. The organic layer was dried and evaporated to obtain a yellow solid as intermediate i-2 (19.01g, 97.6%). 1H NMR (400MHz, CDCl3) δ 9.18 (s, 1H), 8.32-8.29 (m, 1H), 8.29-8.27 (m, 1H), 7.61 (t, J=8.0Hz, 1H).
  • 49
  • [ 2631060-00-7 ]
  • [ 125096-72-2 ]
  • [ 2798771-82-9 ]
YieldReaction ConditionsOperation in experiment
30% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; 1-(8-Bromoquinazolin-4-yl)-3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione (Intermediate CFN) To a solution of 8-bromo-4-chloro-quinazoline (2.00 g, 8.21 mmol, CAS 125096-72-2) and 3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione (2.89 g, 12.3 mmol, Intermediate BTJ) in DMF (25 mL) was added K2CO3(3.41 g, 24.6 mmol), then the mixture was stirred at 60 °C for 10 hours. On completion, the mixture was filtered and the filtrate was extracted with water (200 mL) and EA (150 mL X 3). The combined organic layers was dried over anhydrous Na2SO4, then concentrated in vacuo to give the residue. The residue was purified by reverse-phase (0.1% FA condition) to give the title compound (1.10 g, 30% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 8.37 - 8.35(m, 1H), 8.11 - 8.09 (m, 1H), 7.65 - 7.54 (m, 1H), 7.22 (d, J = 8.8 Hz, 2H), 6.89 - 6.85 (m, 2H), 4.84 (s, 2H), 4.06 (s, 2H), 3.72 (s, 3H), 3.09 - 3.01 (m, 2H). LC-MS (ESI+) m/z 442.9 (M+H)+
30% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; 1-(8-Bromoquinazolin-4-yl)-3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione (Intermediate CFN) To a solution of 8-bromo-4-chloro-quinazoline (2.00 g, 8.21 mmol, CAS 125096-72-2) and 3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione (2.89 g, 12.3 mmol, Intermediate BTJ) in DMF (25 mL) was added K2CO3(3.41 g, 24.6 mmol), then the mixture was stirred at 60 °C for 10 hours. On completion, the mixture was filtered and the filtrate was extracted with water (200 mL) and EA (150 mL X 3). The combined organic layers was dried over anhydrous Na2SO4, then concentrated in vacuo to give the residue. The residue was purified by reverse-phase (0.1% FA condition) to give the title compound (1.10 g, 30% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 8.37 - 8.35(m, 1H), 8.11 - 8.09 (m, 1H), 7.65 - 7.54 (m, 1H), 7.22 (d, J = 8.8 Hz, 2H), 6.89 - 6.85 (m, 2H), 4.84 (s, 2H), 4.06 (s, 2H), 3.72 (s, 3H), 3.09 - 3.01 (m, 2H). LC-MS (ESI+) m/z 442.9 (M+H)+
  • 50
  • [ 1427203-55-1 ]
  • [ 125096-72-2 ]
  • [ 2839750-88-6 ]
YieldReaction ConditionsOperation in experiment
92 % With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; 1.1 Step 1: Preparation of tert-butyl 4-[(2S)-2-[(8-bromoquinazolin-4- yl)amino]propyl]piperazine-l-carboxylate (Intermediate 1) To a solution of 8-bromo-4-chloroquinazoline (10 g, 41 mmol) in MeCN (100 mL) tert-butyl 4-[(2S)-2-aminopropyl]piperazine-l-carboxylate hydrochloride (11.49 g, 41.07 mmol) and then DIPEA (13.27 g, 102.67 mmol) were added. The solution was heated at 40 °C for 2h. After cooling the mixture was concentrated to about 25 mL, water was added (90 mL) and the precipitate was filtered, washed with water (15 mL) and dried under vacuum to afford tert-butyl 4-[(2S)-2-[(8-bromoquinazolin-4- yl)amino]propyl]piperazine-l-carboxylate (17 g, 37.7 mmol, 92% yield) as a white solid. LC-MS (ESI): mlz (M+l): 452.1 (Method 2) NMR (500 MHz, DMSO-d6) d ppm 8.52 (s, 1H), 8.32 (dd, J= 8.4, 1.3 Hz, 1H), 8.12 (dd, J= 7.6, 1.1 Hz, 1H), 8.06 (d, J= 8.0 Hz, 1H), 7.42 (t, J= 7.9 Hz, 1H), 4.67 (spt, (0153) J= 7.0 Hz, 1H), 3.25-3.23 (m, 5H), 2.62-2.57 (m, 2H), 2.43-2.38 (m, 5H), 1.38 (s, 9H), 1.24 (d, J= 6.5 Hz, 3H)
92 % With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; 1.1 Step 1: Preparation of tert-butyl 4-[(2S)-2-[(8-bromoquinazolin-4- yl)amino]propyl]piperazine-l-carboxylate (Intermediate 1) To a solution of 8-bromo-4-chloroquinazoline (10 g, 41 mmol) in MeCN (100 mL) tert-butyl 4-[(2S)-2-aminopropyl]piperazine-l-carboxylate hydrochloride (11.49 g, 41.07 mmol) and then DIPEA (13.27 g, 102.67 mmol) were added. The solution was heated at 40 °C for 2h. After cooling the mixture was concentrated to about 25 mL, water was added (90 mL) and the precipitate was filtered, washed with water (15 mL) and dried under vacuum to afford tert-butyl 4-[(2S)-2-[(8-bromoquinazolin-4- yl)amino]propyl]piperazine-l-carboxylate (17 g, 37.7 mmol, 92% yield) as a white solid. LC-MS (ESI): mlz (M+l): 452.1 (Method 2) NMR (500 MHz, DMSO-d6) d ppm 8.52 (s, 1H), 8.32 (dd, J= 8.4, 1.3 Hz, 1H), 8.12 (dd, J= 7.6, 1.1 Hz, 1H), 8.06 (d, J= 8.0 Hz, 1H), 7.42 (t, J= 7.9 Hz, 1H), 4.67 (spt, (0153) J= 7.0 Hz, 1H), 3.25-3.23 (m, 5H), 2.62-2.57 (m, 2H), 2.43-2.38 (m, 5H), 1.38 (s, 9H), 1.24 (d, J= 6.5 Hz, 3H)
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