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[ CAS No. 2148-55-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2148-55-2
Chemical Structure| 2148-55-2
Chemical Structure| 2148-55-2
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Product Details of [ 2148-55-2 ]

CAS No. :2148-55-2 MDL No. :MFCD09909637
Formula : C8H4Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PCCZEWAQRDIOKD-UHFFFAOYSA-N
M.W : 199.04 Pubchem ID :247911
Synonyms :

Calculated chemistry of [ 2148-55-2 ]

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 : 49.56
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) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 3.13
Log Po/w (WLOGP) : 2.94
Log Po/w (MLOGP) : 2.43
Log Po/w (SILICOS-IT) : 3.21
Consensus Log Po/w : 2.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.66
Solubility : 0.0433 mg/ml ; 0.000217 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.0909 mg/ml ; 0.000456 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.57
Solubility : 0.00542 mg/ml ; 0.0000272 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 2148-55-2 ]

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

Application In Synthesis of [ 2148-55-2 ]

* 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 [ 2148-55-2 ]

[ 2148-55-2 ] Synthesis Path-Downstream   1~21

  • 2
  • [ 104-94-9 ]
  • [ 2393-23-9 ]
  • [ 2148-55-2 ]
  • 4-formyl-3,5-dimethoxyphenoxymethylpolystyrene resin (PAL) [ No CAS ]
  • <i>N</i>4-(4-methoxy-benzyl)-<i>N</i>5-(4-methoxy-phenyl)-quinazoline-4,5-diamine [ No CAS ]
  • 3
  • [ 150-76-5 ]
  • [ 2393-23-9 ]
  • [ 2148-55-2 ]
  • 4-formyl-3,5-dimethoxyphenoxymethylpolystyrene resin (PAL) [ No CAS ]
  • (4-methoxy-benzyl)-[5-(4-methoxy-phenoxy)-quinazolin-4-yl]-amine [ No CAS ]
  • 4
  • [ 10365-98-7 ]
  • [ 2393-23-9 ]
  • [ 2148-55-2 ]
  • 4-formyl-3,5-dimethoxyphenoxymethylpolystyrene resin (PAL) [ No CAS ]
  • (4-methoxy-benzyl)-[5-(3-methoxy-phenyl)-quinazolin-4-yl]-amine [ No CAS ]
  • 5
  • 6,8-dichloro-9-isopropyl-9<i>H</i>-purine [ No CAS ]
  • [ 3934-20-1 ]
  • [ 141-30-0 ]
  • [ 1193-21-1 ]
  • [ 4858-85-9 ]
  • [ 5424-21-5 ]
  • [ 56-05-3 ]
  • [ 1780-31-0 ]
  • [ 2213-63-0 ]
  • [ 607-68-1 ]
  • [ 7253-22-7 ]
  • [ 2148-57-4 ]
  • [ 4752-10-7 ]
  • C17H20NO4Pol [ No CAS ]
  • [ 4774-14-5 ]
  • [ 7148-34-7 ]
  • [ 2148-55-2 ]
  • [ 203436-45-7 ]
  • C21H21ClN3O4Pol [ No CAS ]
  • C21H21ClN3O4Pol [ No CAS ]
  • C21H21ClN3O4Pol [ No CAS ]
  • C21H21ClN3O4Pol [ No CAS ]
  • C21H21ClN3O4Pol [ No CAS ]
  • C22H23ClN3O4Pol [ No CAS ]
  • C22H23ClN3O4Pol [ No CAS ]
  • C21H22ClN4O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H23ClN3O4Pol [ No CAS ]
  • C25H27ClN5O4Pol [ No CAS ]
  • C25H27ClN5O4Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 90℃; for 12h;Combinatorial reaction / High throughput screening (HTS); To a solution of dichloro-heterocycle (S) (15.0 mmol) in n-butanol (200 mL) was added PAL-resin-bound amine 1 (10.0 mmol), followed by addition of diisopropylethylamine (5.2 mL, 30.0 mmol). The suspension was heated to 90[deg.] C. under argon. After 12 hours, the resin was washed by methanol (200 mL*4) and dichloromethane (200 mL*4) and dried under vacuum. The complete conversion of secondary amine (PAL-amine) to tertiary amine was confirmed by bromophenol blue test.
  • 6
  • [ 2148-55-2 ]
  • 4-Anilino-5-chloroquinazoline hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With aniline; In ethanol; EXAMPLE 1 4-Anilino-5-chloroquinazoline hydrochloride (Compound No. 2) A solution of 3.0 g of <strong>[2148-55-2]4,5-dichloroquinazoline</strong> and 1.4 g of aniline in 20 ml of ethanol was heated, whereupon a violet reaction occurred and the reaction mixture solidified. After cooling, the solidified product was collected and recrystallized from ethanol to give 1.8 g (yield 46%) of the desired Compound No.
  • 7
  • [ 1000895-53-3 ]
  • [ 2148-55-2 ]
  • 5-chloro-N-(5-(3,5-dimethoxyphenethyl)-1H-pyrazol-3-yl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; In tetrahydrofuran; at 50.0℃; for 0.5h;Microwave irradiation; General procedure: A mixture of the corresponding 4-chloro quinozoline or quinoline (0.1 mmol), pyrazole amine (0.12 mmol) and 1M HCl (0.05 mmol) in THF (1 mL) was irradiated under microwave condition at 50 C for 30 min. The reaction mixture was partitioned between hydrogen carbonate saturated aqueous solution and dichloromethane, the organic phase was dried oversodium sulfate and concentrated in vacuum, the residue was purified by silica gel chromatography (dichloromethane/MeOH + 10% of aqueous NH3= 10:1) to give the desired product.
  • 8
  • 4-(5-(azetidin-1-yl)-2-(piperidin-2-yl)pyrazolo[1,5-a]pyrimidin-7-yl)morpholine [ No CAS ]
  • [ 2148-55-2 ]
  • 4-(5-(azetidin-1-yl)-2-(1-(5-chloroquinazolin-4-yl)piperidin-2-yl)-pyrazolo[1,5-a]pyrimidin-7-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 80.0℃; for 16.0h; To a solution of intermediate 8 (300 mg, 0.63 mmol) in 2-methoxyethanol (20 mL) was added 4,5-dichioroquinazoline 46 (CAS: 2148552, 1.1 eq., 139 mg, 0.7 mmol) and DIPEA (3 eq., 0.33 mL, 1.9 mmol). The solution was heated to 80C for 16 hours. The solution was concentrated in vacuum, extracted with DCM and washed with water. The combined organics were collected and dried with MgSO4, filtered off and concentratedin vacuum. The crude was purified by column chromatography eluting with a gradient starting from 0 % to 10 % MeOH in DCM. After evaporation compound P35 (190 mg, 57 %) was obtained.LCMS mlz = 505 (M+H)1H NMR (400 MHz, 420 K, DMSO-d6) oe ppm 1.48 - 1.90 (m, 4 H) 2.22 - 2.35 (m, 4 H)3.43 -3.56(m,5H)3.64-3.76(m,4H)3.84(d,J=13.89Hz, 1 H)3.93 -4.04(m,4H)5.18 (s, 1 H) 5.62 (s, 1 H) 5.66 (br. s., 1 H) 7.51 (dd, J=7.16, 1.61 Hz, 1 H) 7.61 - 7.66(m, 1 H) 7.67 - 7.70 (m, 1 H) 8.45 (s, 1 H)
  • 9
  • [ 2148-55-2 ]
  • [ 52721-69-4 ]
  • 5-chloro-N-(2-fluorophenylethyl)-4-aminoquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.3% With triethylamine; In ethanol; for 4.0h;Reflux; General procedure: In a 25 mL three-necked flask, (0.5 mmol) of <strong>[2148-55-2]4,5-dichloroquinazoline</strong> was added,0. 75 mmol Trifluoro-phenethylamine, 6 mL of ethanol and 3 to 4 drops of triethylamine, reaction under reflux for 4 h,TLC tracking to the point of no raw materials, stop the reaction, column chromatography separation, obtained milky white solid, yield 86. 2%; As in Example 1 (3) Synthesis step and process conditions,The difference is that <strong>[2148-55-2]4,5-dichloroquinazoline</strong>,The molar ratio of 2-fluorophenethylamine to ethanol was 1: 1. 55: 1.25 per 0.5 mmol<strong>[2148-55-2]4,5-dichloro-quinazoline</strong> drops of triethylamine 6 drops,Reaction time 4 h, a yellow solid, yield 66. 3%
  • 11
  • [ 2148-55-2 ]
  • [ 57260-71-6 ]
  • 4-(N-Βοc piperazine)-5-chloroquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydride; In N,N-dimethyl-formamide; at 20.0℃; for 8.0h; In a 25 mL three-necked flask, (1.5 mmol) of <strong>[2148-55-2]4,5-dichloroquinazoline</strong> was added(1.8 mmol) of N-Boc piperazine as well 6 mL of anhydrous N,N-dimethylformamide,2. 25 mmol sodium hydride mixed at room temperature for 8 h, The reaction mixture was quenched, washed with saturated ammonium chloride solution, extracted with methylene chloride, stripped off and purified by column chromatography to give 0.45 g of an oily product in a yield of 86.0%
  • 12
  • [ 60233-66-1 ]
  • [ 2148-55-2 ]
YieldReaction ConditionsOperation in experiment
65.8% With triethylamine; trichlorophosphate; for 8.0h;Reflux; To a 50 mL three-necked flask was charged 1.00 g (5.42 mmol) of 5-chloroquinazolin-4(3H) -one, Add 13.0 mL of POCl3 and 6 mL of triethylamine. Heat the mixture to reflux for 8h. Remove the excess POCl3 by distillation under reduced pressure. Cool and add 30 mL of CH2C12 to the reaction solution under ice-cooling, then slowly pour the CH2C12 solution into 33 ML 1mol / L of ice hydrochloric acid, and then 33 mL 1 mol / L of ice hydrochloric acid washing reactor,The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was stirred with anhydrous K2CO3 until the pH was neutral, filtered and concentrated under reduced pressure.Column chromatography gave the product 0.71 g,The yield was 65.8%, m.p. 135-138 C (131.5-133 C)
54.4% With triethylamine; trichlorophosphate; In toluene; at 120.0℃; for 5.0h; 5-chloroquinazolin-4(3H)-one (11.0 mmol) was placed in a 100 mL round bottom flask, 20 mL of toluene was added thereto and stirred to dissolve, and then 5 equivalents of POCl3 and 2 equivalents of triethylamine were added to the system, and heated to After refluxing at 120 C, the reaction was stopped after 5 h of reaction, and the solution was dissolved. The solid was dissolved in 100 ml of LDCM, adjusted to pH 6-7 with aqueous ammonia, washed with water (30 mL*3), and purified by column chromatography (PE: EA = 10:1). White solid, yield 54.4%.
54.4% With triethylamine; trichlorophosphate; In toluene; at 120.0℃; for 5.0h; Place 5-chloroquinazoline-4 (3H) -one (11.0 mmol) in a 100 mL round bottom flask,20 mL of toluene was added thereto to stir and dissolve, and 5 equivalents of POCl3 and2 equivalents of triethylamine, heated to 120 C and refluxed, the reaction was stopped after 5h, and the solvent was dissolved.Dissolve the solid with 100mL of DCM, adjust the pH to 6-7 with ammonia, and wash with water (30mL * 3).Purification by column chromatography (PE: EA = 10: 1 V / V), a white solid was obtained with a yield of 54.4%.
  • 13
  • [ 2148-55-2 ]
  • 5-chloro-4-(4-benzylpiperazin-1-yl)quinazoline [ No CAS ]
  • 14
  • [ 2148-55-2 ]
  • 5-chloro-4-(4-(4-chlorobenzyl)piperazin-1-yl)quinazoline [ No CAS ]
  • 15
  • [ 2148-55-2 ]
  • 5-chloro-4-(4-(4-fluorobenzyl)piperazin-1-yl)quinazoline [ No CAS ]
  • 16
  • [ 2148-55-2 ]
  • 4-piperazin-5-chloroquinazoline [ No CAS ]
  • 17
  • [ 404-70-6 ]
  • [ 2148-55-2 ]
  • 5-chloro-N-(3-fluorophenylethyl)-4-aminoquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.2% With triethylamine; In ethanol; for 4h;Reflux; In a 25 mL three-necked flask, (0.5 mmol) of 4,5-dichloroquinazoline was added,0. 75 mmol Trifluoro-phenethylamine, 6 mL of ethanol and 3 to 4 drops of triethylamine, reaction under reflux for 4 h,TLC tracking to the point of no raw materials, stop the reaction, column chromatography separation, obtained milky white solid, yield 86. 2%;
  • 18
  • [ 120-20-7 ]
  • [ 2148-55-2 ]
  • 5-chloro-N-(3,4-dimethoxyphenylethyl)-4-aminoquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.5% With triethylamine; In ethanol; for 5.0h;Reflux; General procedure: In a 25 mL three-necked flask, (0.5 mmol) of <strong>[2148-55-2]4,5-dichloroquinazoline</strong> was added,0. 75 mmol Trifluoro-phenethylamine, 6 mL of ethanol and 3 to 4 drops of triethylamine, reaction under reflux for 4 h,TLC tracking to the point of no raw materials, stop the reaction, column chromatography separation, obtained milky white solid, yield 86. 2%; As in Example 1 (3), conditions and methods were synthesized,The difference is that <strong>[2148-55-2]4,5-dichloroquinazoline</strong>,The molar ratio of 3,4-dimethoxyphenethylamine to ethanol was1: 1.45: 1.15, 4 drops of triethylamine per 0.5 mmol of <strong>[2148-55-2]4,5-dichloroquinazoline</strong>, Reaction time 5h, the yield was 79.5%.
  • 19
  • [ 617-89-0 ]
  • [ 2148-55-2 ]
  • 5-chloro-N-(furan-2-methyl)quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.9% With triethylamine; In isopropyl alcohol; at 80.0℃; for 1.0h; 5-chloroquinazoline (5 mmol) was added to a 50 mL round bottom flask, and 20 mL of dry isopropanol was added to stir and dissolve. Then 1.5 equivalents of triethylamine and 1.2 equivalents of 2-furanmethylamine were added, and the reaction was stopped after reacting at 80 C for 1 h. , desolvation, column chromatography (eluent PE: EA = 15:1) gave a white solid.
  • 20
  • [ 2148-55-2 ]
  • 5-chloro-N-(furan-2-methyl)-N-methylquinazolin-4-amine [ No CAS ]
  • 21
  • [ 2148-55-2 ]
  • C15H14ClN3O [ No CAS ]
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