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[ CAS No. 264208-72-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 264208-72-2
Chemical Structure| 264208-72-2
Chemical Structure| 264208-72-2
Structure of 264208-72-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 264208-72-2 ]

CAS No. :264208-72-2 MDL No. :MFCD12828182
Formula : C16H20ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XAVZTXQALXOZJS-UHFFFAOYSA-N
M.W : 321.80 Pubchem ID :11782230
Synonyms :

Calculated chemistry of [ 264208-72-2 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.5
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 91.07
TPSA : 47.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.43
Log Po/w (XLOGP3) : 3.23
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 2.0
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0367 mg/ml ; 0.000114 mol/l
Class : Soluble
Log S (Ali) : -3.9
Solubility : 0.0405 mg/ml ; 0.000126 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.08
Solubility : 0.0027 mg/ml ; 0.00000839 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.37

Safety of [ 264208-72-2 ]

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 [ 264208-72-2 ]

* 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 [ 264208-72-2 ]

[ 264208-72-2 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 452-80-2 ]
  • [ 264208-72-2 ]
  • 4-(2-fluoro-4-methylanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Example 6 A suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (200mg, 0.622mmol), (prepared as described for the starting material in Example 2c) and <strong>[452-80-2]2-fluoro-4-methylaniline</strong> (94mg, 0.764mmol) in isopropanol (5ml) containing 6.2M hydrogen chloride in isopropanol (110mul) was stirred at 80°C for 1.5 hours. After cooling, the precipitate was collected by filtration, washed with isopropanol, followed by ether and dried under vacuum. The solid was purified by column chromatography, eluding with methylene chloride/methanol (90/10) followed by 5 percent ammonia in methanol/methylene chloride (10/90). Evaporation of the fractions containing the expected product gave 4-(2-fluoro-4-methylanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (170mg, 61percent). MS - ESI: 411 [MH]+ 1H NMR Spectrum: (DMSOd6) 1.3-1.45 (m, 2H), 1.8 (d, 2H), 1.7-1.9 (m, 1H), 1.9 (t, 2H), 2.2 (s, 3H), 2.35 (s, 3H), 2.8 (d, 2H), 3.95 (s, 3H), 4.01 (d, 2H), 7.1 (d, 1H), 7.13 (d, 1H), 7.16 (s, 1H), 7.4 (t, 1H), 7.81 (s, 1H), 8.32 (s, 1H), 9.4 (s, 1H)
  • 2
  • [ 84478-72-8 ]
  • [ 264208-72-2 ]
  • 2-chloro-4-fluoro-5-[6-methoxy-7-(1-methyl-piperidin-4-ylmethoxy)-quinazolin-4-ylamino]-phenol [ No CAS ]
  • 3
  • [ 67567-26-4 ]
  • [ 264208-72-2 ]
  • 4-(4-bromo-2,6-difluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Example 4 Under argon, sodium hydride (60percent, 372mg, 9.3mmol) was added to a solution of <strong>[67567-26-4]4-bromo-2,6-difluoroaniline</strong> (1.67g, 8.08mmol) in DMF. After stirring for 30 minutes at ambient temperature, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (1.3g, 4.04mmol) was added and stirring was continued for a further 20 hours. The mixture was poured onto water (130ml) and extracted with ethyl acetate. The organic layers were washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by column chromatography on silica, eluding with methylene chloride/methanol (95/5) followed by methylene chloride/methanol containing ammonia (1percent) (90/10). The fractions containing the expected product were combined and evaporated. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum at 50°C to give 4-(4-bromo-2,6-difluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (1.4g, 70percent). MS - ESI: 493-495 [MH]+ 1H NMR Spectrum: (DMSOd6) 1.3-1.45 (m, 2H), 1.8 (d, 2H), 1.7-1.9 (m, 1H), 1.9 (t, 2H), 2.17 (s, 3H), 2.8 (d, 2H), 3.95 (s, 3H), 4.02 (d, 2H), 7.2 (s, 1H), 7.63 (s, 1H), 7.6 (s, 1H), 7.82 (s, 1H), 8.35 (s, 1H)
  • 4
  • [ 69411-06-9 ]
  • [ 264208-72-2 ]
  • 4-(4-chloro-2,6-difluoroanilino)-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline [ No CAS ]
  • 5
  • [ 2401-24-3 ]
  • [ 264208-72-2 ]
  • M 475271 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride In isopropyl alcohol at 80℃;
  • 6
  • [ 635678-09-0 ]
  • [ 264208-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: hydrogen / palladium on activated carbon / methanol 3: 2-methoxy-ethanol / 2 h / 115 °C 4: oxalyl chloride / CHCl3; dimethylformamide / Heating
Multi-step reaction with 4 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating
Multi-step reaction with 4 steps 1: trifluoroacetic acid; nitric acid / dichloromethane / 0.01 h / 20 °C / Cooling with ice 2: palladium on activated charcoal; hydrogen / methanol / 6 h 3: 2-methoxy-ethanol / 3.67 h / 120 °C 4: N,N-dimethyl-formamide; thionyl chloride / 0.12 h / 20 °C / Cooling with ice
  • 7
  • [ 72107-05-2 ]
  • [ 264208-72-2 ]
  • 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yloxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
17 Example 17 Example 17 Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13g, 0.4mmol), (prepared as described for the starting material in Example 10), was reacted with 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol (95mg, 0.5mmol), (IZV. ACAD. NAVK. SSSR. Ser. Khim. 1981, 9, 2008), to give 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(2,2,4-trimethyl-1,2-dihydroquinolin-6-yloxy)quinazoline (140mg, 74%). 1H NMR Spectrum: (DMSOd6) 1.15(s, 6H); 1.3-1.45(m, 2H); 1.7-2.0(m, 8H); 2.16(s, 3H); 2.65-2.85(d, 2H); 4.0(s, 3H); 4.05(d, 2H); 5.35(s, 1H); 5.9(s, 1H); 6.5(d, 1H); 6.80(d, 1H); 6.82(s, 1H); 7.33(s, 1H); 7.5(s, 1H); 8.52(s, 1H) MS (ESI): 475 [MH]+
  • 8
  • [ 13314-85-7 ]
  • [ 264208-72-2 ]
  • 6-methoxy-4-(2-methylindol-5-yloxy)-7-((1-methylpiperidin-4-yl)methoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 11 Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13g, 0.4mmol), (prepared as described for the starting material in Example 10), was reacted with <strong>[13314-85-7]5-hydroxy-2-methylindole</strong> (74mg, 0.5mol) to give 6-methoxy-4-(2-methylindol-5-yloxy)-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (137mg, 79%). 1H NMR Spectrum: (DMSOd6) 1.3-1.45(m, 2H); 1.7-1.95(m, 5H); 2.15(s, 3H); 2.4(s, 3H); 2.8(d, 2H); 3.98(s, 3H); 4.05(d, 2H); 6.14(s, 1H); 6.88(d, 1H); 7.29(s, 1H); 7.32(d, 1H); 7.35(s, 1H); 7.6(s, 1H); 8.45(s, 1H) MS (ESI): 433 [MH]+
  • 9
  • [ 165112-03-8 ]
  • [ 264208-72-2 ]
  • 6-methoxy-4-(2-methylquinolin-7-yloxy)-7-((1-methylpiperidin-4-yl)methoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
46 Example 46 Example 46 Using an analogous procedure to that described in Example 42, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (100mg, 0.31mmol), (prepared as described for the starting material in Example 10), was reacted with 7-hydroxy-2-methylquinoline (54mg, 0.34mmol), (J. Med. Chem. 1998, 41 , 4062), to give 6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)-4-(2-methylquinolin-7-yloxy)quinazoline (86mg, 63%). MS - ESI: 445 [MH]+ 1H NMR Spectrum: (CDCl3) 1.4-1.6 (m, 2H); 1.95 (d, 2H); 2.05 (t, 2H); 1.9-2.1 (m, 1H); 2.35 (s, 3H); 2.8 (s, 3H); 2.95 (d, 2H); 4.1 (s, 3H); 4.15 (d, 2H); 7.3 (m, 2H); 7.45 (dd, 1H); 7.6 (s, 1H); 7.9 (d, 1H); 7.95 (s, 1H); 8.1 (d, 1H); 8.6 (s, 1H)
  • 10
  • [ 41292-66-4 ]
  • [ 264208-72-2 ]
  • 6-methoxy-4-(2-methyl-1H-benzimidazol-6-yloxy)-7-((1-methylpiperidin-4-yl)methoxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonia; In methanol; dichloromethane; Example 190 Using an analogous procedure to that described in Example 189, 4-chloro-6-methoxy-7-(1-methylpiperidin-4-yl)methoxyquinazoline, (prepared as described for the starting material in Example 10), was reacted with <strong>[41292-66-4]5-hydroxy-2-methylbenzimidazole</strong> (200 mg, 0.62 mmol) and after work-up and purification on a 10 g silica ISOLUTE column using successively dichloromethane, dichloromethane/methanol (95/5) and dichloromethane/methanol saturated with ammonia (95/5), gave 6-methoxy-4-(2-methyl-1H-benzimidazol-6-yloxy)-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (68 mg, 25%). 1H NMR Spectrum: (DMSOd6 + TFA) 1.60 (m, 2H); 2.10 (m, 2H); 2.20 (m, 1H); 2.80 (s, 3H); 2.85 (s, 3H); 3.05 (m, 2H); 3.50 (m, 2H); 4.05 (s, 3H); 4.15 (d, 2H); 7.50 (s, 1H); 7.55 (d, 1H); 7.70 (s, 1H); 7.85 (d, 1H); 7.90 (d, 1H); 8.65 (s, 1H) MS (ESI): 434 [MH]+
  • 11
  • [ 15463-09-9 ]
  • [ 264208-72-2 ]
  • 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(4-methylquinolin-7-yloxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 13 Using a procedure analogous to that described for Example 10, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (130mg, 0.4mmol), (prepared as described for the starting material in Example 10), was reacted with 4-methyl-7-hydroxyquinoline (80mg, 0.5mol), (Chem. Ber. 1967, 100, 2077), to give 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(4-methylquinolin-7-yloxy)quinazoline (160mg, 90%). 1H NMR Spectrum: (DMSOd6) 1.3-1.5(m, 2H); 1.7-1.95(m, 3H); 1.9(t, 2H); 2.17(s, 3H); 2.74(s, 3H); 2.8(d, 2H); 4.07(s, 3H); 4.1(d, 2H); 7.4(m, 2H); 7.65(dd, 1H); 7.65(s, 1H); 7.9(s, 1H); 8.21(d, 1H); 8.54(s, 1H); 8.78(d, 1H) MS (ESI): 445 [MH]+
  • 12
  • [ 580-20-1 ]
  • [ 264208-72-2 ]
  • 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(quinolin-7-yloxy)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonia; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3h; Example 10 A suspension of 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (74mg, 0.23mmol), potassium carbonate (48mg, 0.35mmol) and <strong>[580-20-1]7-hydroxyquinoline</strong> (40.6mg, 0.28mmol) in DMF (1.5ml) was heated at 100C for 3 hours. After cooling, the mixture was stirred for 10 hours at ambient temperature and then overnight at 5C. After dilution with methylene chloride (5ml), the mixture was poured onto a column of silica and was eluted with an increasing gradient of methanol/methylene chloride (10/90, 20/80) followed by ammonia/methanol (5%) in methylene chloride (25/75) to give, after removal of the volatiles by evaporation and drying under vacuum, 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-4-(quinolin-7-yloxy)quinazoline (82mg, 88%). 1H NMR Spectrum: (DMSOd6) 1.3-1.5(m, 2H); 1.75-1.9(m, 3H); 1.9-2.05(m, 2H); 2.12(s, 3H); 2.8-2.9(d, 2H); 4.5(s, 3H); 4.1(d, 2H); 7.4(s, 1H); 7.6(dd, 1H); 7.62(dd, 1H) MS (ESI): 431 [MH]+
  • 13
  • [ 367-24-8 ]
  • [ 264208-72-2 ]
  • [ 443913-73-3 ]
  • 14
  • [ 20691-89-8 ]
  • [ 264208-72-2 ]
  • 15
  • [ 56962-01-7 ]
  • [ 264208-72-2 ]
  • 2-chloro-3-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.4% With hydrogenchloride; In water; acetonitrile; at 130℃; for 1h;Microwave irradiation; Example 213 - -Chloro-3-((6-methoxy-7-((1 -methyl pi peridi n-4-yl)methoxy)qui nazol i n-4- yl)amino)phenol was prepared (3 mg, off-white solid, 1 .4% yield).[00766] 4-Chloro-6-methoxy-7-[(1 -methyl-4-piperidinyl)methoxy]quinazoline (64 mg, 0.20 mmol) and <strong>[56962-01-7]3-amino-2-chlorophenol</strong> (72 mg, 0.50 mmol) were mixed with MeCN (6 mL) and 2drops of conc. HCI and heated in the microwave at 130 00 for 1 h. The reaction mixture was concentrated, diluted with water, basified with aqueous sodium carbonate and extracted with EtOAc (x3). The combined extracts were concentrated and the residue purified by prep hplc to give the title compound.[00767] LCMS: Low_pH_2min RT 0.56mm, purity >95%, [M-H] 427.2. High_pH_2min RT0.84mm, purity >95%, [M-H] 427.2.[00768] 1H NMR (300 MHz, DMSO-d6): O 1.29 - 1.47 (m, 2 H), 1.73 - 1.89 (m, 3 H), 1.94- 2.06 (m, 2 H), 2.23 (5, 3 H), 2.82 - 2.92 (m, 2 H), 3.94 (5, 3 H), 4.00 (d, J=6.0 Hz, 2 H), 6.89-7.00 (m, 2 H), 7.14-7.22 (m, 2 H), 7.82 (5, 1 H), 8.21 (5, 1 H), 8.28 (5, 1 H), 9.43 (br 5, 1 H).
  • 16
  • [ 53222-92-7 ]
  • [ 264208-72-2 ]
  • 3-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)-2-methylphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; acetonitrile; at 130℃; for 1h;Microwave irradiation; Example 212 - 3-((6-Methoxy-7-((1 -methyl pi peridi n-4-yl)methoxy)qui nazol i n-4-yl)ami no)-2- methylphenol was prepared (5 mg, pink solid, 2.5% yield).[00763] 4-Chloro-6-methoxy-7-[(1 -methyl-4-piperidinyl)methoxy]quinazoline (64 mg, 0.20mmol), 3-amino-2-methylphenol (366 mg, 0.50 mmol) and 3 drops of conc HCI were mixed withMeCN (21 mL) and heated in the microwave at 130 00 for 1 h. The reaction mixture wasconcentrated, diluted with water, basified with aqueous sodium carbonate and extracted with 0H2012 (x3). The combined extracts were concentrated and the residue purified by prep hplc to give the title compound.[00764] LCMS: LowpH_2min RT 0.54mm, purity 90-95%, [M-H] 407.2. HighpH_2minRT 1 .02mm, purity >95%, [M-H] 407.2.[00765] 1H NMR (300 MHz, DMSO-d6): O 1.29 - 1.47 (m, 2 H), 1.72 - 1.90 (m, 3 H), 1.95(5, 3 H), 1.97-2.12 (m, 2 H), 2.25 (5, 3 H), 2.83-2.94 (m, 2 H), 3.92 (5, 3 H), 4.00 (d, J=6.0Hz, 2 H), 6.80 (t, J=7.6 Hz, 2 H), 7.00 (t, J=7.6 Hz, 1 H), 7.14 (5, 1 H), 7.81 (5, 1 H), 8.20 (5, 1H), 8.24 (5, 1 H), 9.33 (br 5, 1 H).
  • 17
  • [ 20691-89-8 ]
  • [ 263400-68-6 ]
  • [ 264208-72-2 ]
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