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[ CAS No. 953039-15-1 ] {[proInfo.proName]}

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Chemical Structure| 953039-15-1
Chemical Structure| 953039-15-1
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Product Details of [ 953039-15-1 ]

CAS No. :953039-15-1 MDL No. :MFCD09907933
Formula : C9H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :AYOXOMXNWRXDGY-UHFFFAOYSA-N
M.W : 194.62 Pubchem ID :55251455
Synonyms :

Calculated chemistry of [ 953039-15-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.04
TPSA : 35.01 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) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.28
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.11

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.226 mg/ml ; 0.00116 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.525 mg/ml ; 0.0027 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0164 mg/ml ; 0.0000841 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 953039-15-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 953039-15-1 ]

* 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 [ 953039-15-1 ]

[ 953039-15-1 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 91099-24-0 ]
  • [ 953039-15-1 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate for 6h; Heating / reflux; 4.4 Step 4. Preparation of 2-Chloro-7-methoxyquinazoline The crude 2-Hydroxy-7-methoxyquinazoline (12.48 g) was mixed with 170 mL of POCI3, and the reaction mixture was stirred under reflux conditions for 6 hours. POCI3 was removed using a PP028218.0002rotovap. The crude was mixed with ~500 inL of CHCI3, stirred for 1 hour at RT, neutralized with Na2COa (pH 6-7) and the product was then extracted into chloroform. The emulsion that formed was filtered through celite, organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude was purified by column chromatography (EtOAc/Hex) followed by recrystallization from EtO Ac/Hex giving 4.4g of pure compound 6 (the combined yield for two last steps is 29%).
  • 2
  • [ 953039-15-1 ]
  • [ 98-18-0 ]
  • 3-(7-methoxyquinazolin-2-ylamino)benzenesulfonamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol at 90℃; for 20h; 4.5 Step 5. Preparation of 3-(7-Methoxyquinazolin-2-ylamino)benzenesulfonamide To a 0.3 M solution of 2-chloro-7-methoxyquinazoline 6 in 2-propanol was added sulfanilamide (1.0 eq). The reaction was stirred at 90 0C for 20 hours. The hydrochloride was collected by vacuum filtration and then stirred in aqueous sodium bicarbonate. The solid was collected by vacuum filtration and rinsed with water. The off-white solid was dried in vacuum to give the desired product in 95% yield. ES/MS m/z 331 (MH+).
  • 3
  • [ 953039-15-1 ]
  • [ 21626-70-0 ]
  • 7-methoxy-N-(4-morpholin-4-ylsulfonyl-phenyl)quinazolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In isopropyl alcohol at 80℃; 37.1 Example 37Synthesis of N- (4-(morpholinosulfonyl) phenyl-7- (pperidin-4-yloxy) quinazolin-2 -amine(Compound 332)Step 1. Preparation of 7-methoxy-N- (4-(morpholinosulfonyl) phenyl) quinazolin-2-amine A mixture of 2-chloro-7-methoxyquinazoline (leq) and 4-(Mθφholinosulfonyl) Aniline (leq) in 2-propanol was heated at 8O0C overnight. Product was precipitated in the reaction mixture. The precipitate was filtered, washed and dried under vacuum to provide 7-methoxy-N- (4- PP028218.0002(morpholinosulfonyl) phenyl) quinazolin-2-amine as a yellow solid in 99% yield. ES/MS m/z 401.0(MH+).
  • 4
  • [ 953039-15-1 ]
  • [ 953039-98-0 ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: ethanethiol With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; Stage #2: 2-chloro-7-methoxyquinazoline In dichloromethane at 0 - 20℃; for 2h; 42.1 Example 42Synthesis of 5-(7-(piperidin-4-yloxy)-quinazolin-2-ylamino]- lH-benzo[d] imidazol-2 (3H)-one (Compound 330)Step 1. Preparation of 2-(ethylthio) quinazolin-7-olTo a solution of ethanthiol (30ml) in DCM (50ml) was added AICI3 (6eq). The reaction mixture was cooled to 00C and stirred for lOmin under N2 atmosphere. A solution of 2-chloro-7- methoxyquinazoline (leq) in DCM (20ml) was added dropwise to it. The reaction mixture was warmed to room temperature and stirred for 2h. The solvent was evaporated and residue was partitioned between EtOAc and satd. NaHCO3. The insoluble material was filtered, washed and dried to provide title product as a yellow solid (yield, 60%). The ethyl acetate layer was separated from basic layer, washed with brine and dried over sodium sulfate. Filtration, PP028218.0002evaporation and drying under vacuum provide additional amount of product, (yield, 38%) . ES/MS m/z 207.0 (MH+).
  • 5
  • [ 953039-15-1 ]
  • [ 75-08-1 ]
  • 2-ethylthio-7-methoxy-quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 36h; 58.1 Example 58Synthesis of 4-(7-(2-fluoropyridin-4-yloxy)quinaz»lin-2-ylainino)benzenesulfonainide (Compound 416)Step 1. To a solution of DCM/ethanethiol (0.3 M, 1:1) was added AlCl3 (6 eq.) and the reaction was cooled to 0 0C under a nitrogen atmosphere. Compound 6 was dissolved in DCM and added dropwise to the above solution dropwise. The reaction was allowed to warm to room temperature and stirred for 36 hr. The solvent was removed under vacuum and the crude was dissolved in EtOAc. Saturated NaHCO3 was added slowly dropwise and the layers were separated. The organic layer was dried with brine and Na2SO4 and concentrated. The crude was triturated in DCM and the precipitate was filtered off to give the desired product as an off-white solid in 83% yield. ES/MS m/z 207.0 (MH+).
  • 6
  • [ 953039-66-2 ]
  • [ 124-41-4 ]
  • [ 953039-15-1 ]
YieldReaction ConditionsOperation in experiment
With copper(I) bromide; In methanol; N,N-dimethyl-formamide;Inert atmosphere; Reflux; step one:<strong>[953039-66-2]2-chloro-7-bromoquinazoline</strong> (8.11 mmol) was dissolved in N, N-dimethylformamide (10 mL)Under argon atmosphere, cuprous bromide (10.16 mmol)Sodium methoxide (40.54 mmol, 5.4 M in MeOH)Followed by addition of the above solution.Heated to reflux mass spectrometry to no raw material remaining,Stop the reaction.After cooling to room temperature, the solvent was removed in vacuo and the residue was taken up with ethyl acetate. The resulting organic phase was washed three times with water until the solution was light blue and washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated by filtration to give the title compoundQ.
  • 7
  • [ 953039-15-1 ]
  • C8H5ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron trichloride In dichloromethane at -78℃; 99.2 Step two:The above compound Q (7.98 mmol) was dissolved in dichloromethane (100 mL)After cooling to -78 ° C,A solution of boron trichloride in dichloromethane (1.0 M, 25 mL) was slowly added to the above reaction solution,Reaction to mass spectrometry after the absence of raw materials,Stop the reaction.The reaction solution was quenched with saturated ammonium chloride solution, and the resulting dichloromethane was washed with saturated brine, dried over anhydrous magnesium sulfate,The crude product R obtained after filtration and concentrated was used directly in the next step.
  • 8
  • [ 953039-15-1 ]
  • 3-(7-hydroxyquinazolin-2-ylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 20 h / 90 °C 2.1: water; sodium hydrogencarbonate 3.1: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 3 h / 20 - 80 °C 3.2: pH 6
  • 9
  • [ 953039-15-1 ]
  • 3-(7-methoxyquinazolin-2-ylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: isopropyl alcohol / 20 h / 90 °C 2: water; sodium hydrogencarbonate
  • 10
  • [ 953039-15-1 ]
  • [ 953039-93-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: isopropyl alcohol / 80 °C 2: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C
  • 11
  • [ 953039-15-1 ]
  • 4-(7-(2-fluoro-pyridin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aluminum (III) chloride / dichloromethane / 36 h / 0 - 20 °C 2: triethylamine / copper diacetate / dichloromethane / 24.08 h / 20 °C / Molecular sieves 4Å 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C 4: toluene-4-sulfonic acid / 1,4-dioxane / 15 h / 100 °C
  • 12
  • [ 953039-15-1 ]
  • 7-piperidin-4-yloxy-N-(3-trifluoromethyl-phenyl)-quinazolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: Oxone / tetrahydrofuran; water / 4.5 h / 0 - 20 °C 4.1: 16 h / 100 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h
  • 13
  • [ 953039-15-1 ]
  • 3-(7-(1-methylpiperidin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: isopropyl alcohol / 20 h / 90 °C 2.1: water; sodium hydrogencarbonate 3.1: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 3 h / 20 - 80 °C 3.2: pH 6 4.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 4.2: 10 h / 20 °C
  • 14
  • [ 953039-15-1 ]
  • 5-(7-piperidin-4-yloxy-quinazolin-2-ylamino)-1,3-dihydro-benzo[d]imidazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: Oxone / tetrahydrofuran; water / 4.5 h / 0 - 20 °C 4.1: acetonitrile / 48 h / 110 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
  • 15
  • [ 953039-15-1 ]
  • 7-(1-isopropyl-piperidin-4-yloxy)-N-(3-trifluoromethyl-phenyl)-quinazolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: Oxone / tetrahydrofuran; water / 4.5 h / 0 - 20 °C 4.1: 16 h / 100 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h 6.1: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C
  • 16
  • [ 953039-15-1 ]
  • 7-(1-methyl-1H-pyrazol-4-yl)-N-(4-(morpholine-4-sulfonyl)-phenyl)-quinazolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: isopropyl alcohol / 80 °C 2: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C 3: 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine / 20 °C 4: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 0.17 h / 120 °C / Microwave irradiation
  • 17
  • [ 953039-15-1 ]
  • N-(4-(morpholine-4-sulfonyl)phenyl)-7-piperidin-4-yloxy-quinazolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: isopropyl alcohol / 80 °C 2.1: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C 3.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 3.2: 20 °C 4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
  • 18
  • [ 953039-15-1 ]
  • N7-(1-methyl-piperidin-4-yl)-N2-(4-(morpholine-4-sulfonyl)phenyl)quinazoline-2,7-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: isopropyl alcohol / 80 °C 2: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C 3: 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine / 20 °C 4: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 3 h / 110 °C
  • 19
  • [ 953039-15-1 ]
  • tert-butyl 4-(2-(3-trifluoromethyl-phenylamino)-quinazolin-7-yloxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: Oxone / tetrahydrofuran; water / 4.5 h / 0 - 20 °C 4.1: 16 h / 100 °C
  • 20
  • [ 953039-15-1 ]
  • tert-butyl 4-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-ylamino)quinazolin-7-yloxy)-piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: Oxone / tetrahydrofuran; water / 4.5 h / 0 - 20 °C 4.1: acetonitrile / 48 h / 110 °C
  • 21
  • [ 953039-15-1 ]
  • 7-(1-(2-fluoroethyl)-piperidin-4-yloxy)-N-(4-(morpholine-4-sulfonyl)phenyl)-quinazolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: isopropyl alcohol / 80 °C 2.1: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C 3.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 3.2: 20 °C 4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
  • 22
  • [ 953039-15-1 ]
  • tert-butyl 4-(2-(4-(morpholin-4-ylsulfonyl)phenylamino)quinazolin-7-yloxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: isopropyl alcohol / 80 °C 2.1: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C 3.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 3.2: 20 °C
  • 23
  • [ 953039-15-1 ]
  • 4-(7-(2-fluoro-pyridin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: aluminum (III) chloride / dichloromethane / 36 h / 0 - 20 °C 2: triethylamine / copper diacetate / dichloromethane / 24.08 h / 20 °C / Molecular sieves 4Å 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C 4: toluene-4-sulfonic acid / 1,4-dioxane / 15 h / 100 °C 5: water; acetonitrile / 48 h
  • 24
  • [ 953039-15-1 ]
  • [ 953040-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 36 h / 0 - 20 °C 2: triethylamine / copper diacetate / dichloromethane / 24.08 h / 20 °C / Molecular sieves 4Å
  • 25
  • [ 953039-15-1 ]
  • [ 953040-49-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 36 h / 0 - 20 °C 2: triethylamine / copper diacetate / dichloromethane / 24.08 h / 20 °C / Molecular sieves 4Å 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C
  • 26
  • [ 953039-15-1 ]
  • [ 953039-99-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C
  • 27
  • [ 953039-15-1 ]
  • [ 953040-00-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C 1.2: 2 h / 0 - 20 °C 2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 20 °C 3.1: Oxone / tetrahydrofuran; water / 4.5 h / 0 - 20 °C
  • 28
  • [ 953039-15-1 ]
  • [ 953039-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: isopropyl alcohol / 80 °C 2: 1-methyl-pyrrolidin-2-one; sodium thiomethoxide / 4 h / 80 °C 3: 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine / 20 °C
  • 29
  • [ 17484-36-5 ]
  • [ 953039-15-1 ]
  • 30
  • [ 22996-21-0 ]
  • [ 953039-15-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; iron; acetic acid / ethanol; water / 1 h / 60 - 65 °C 2: 1 h / 160 - 180 °C 3: trichlorophosphate / 6 h / Heating / reflux
  • 31
  • [ 59236-36-1 ]
  • [ 953039-15-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1 h / 160 - 180 °C 2: trichlorophosphate / 6 h / Heating / reflux
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