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[ CAS No. 162363-46-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 162363-46-4
Chemical Structure| 162363-46-4
Chemical Structure| 162363-46-4
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Product Details of [ 162363-46-4 ]

CAS No. :162363-46-4 MDL No. :MFCD06657617
Formula : C12H13ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HGMQPDNSSYTATF-UHFFFAOYSA-N
M.W : 252.70 Pubchem ID :11687474
Synonyms :

Calculated chemistry of [ 162363-46-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.15
TPSA : 44.24 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) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.89
Log Po/w (XLOGP3) : 3.18
Log Po/w (WLOGP) : 3.08
Log Po/w (MLOGP) : 1.81
Log Po/w (SILICOS-IT) : 3.23
Consensus Log Po/w : 2.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.0662 mg/ml ; 0.000262 mol/l
Class : Soluble
Log S (Ali) : -3.78
Solubility : 0.0419 mg/ml ; 0.000166 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.01
Solubility : 0.00245 mg/ml ; 0.00000968 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.98

Safety of [ 162363-46-4 ]

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 [ 162363-46-4 ]

* 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 [ 162363-46-4 ]

[ 162363-46-4 ] Synthesis Path-Downstream   1~67

  • 1
  • [ 131865-54-8 ]
  • [ 162363-46-4 ]
  • 4-(4'-[18F]fluorobenzylamino)-6,7-diethoxyquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Proton Sponge In N,N-dimethyl-formamide at 140℃; for 1h;
  • 4
  • [ 372-19-0 ]
  • [ 162363-46-4 ]
  • 6,7-diethoxy-4-(3-fluoroanilino)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 5
  • [ 367-21-5 ]
  • [ 162363-46-4 ]
  • (3-chloro-4-fluoro-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 6
  • [ 54060-30-9 ]
  • [ 162363-46-4 ]
  • 6,7-diethoxyquinazolin-4-yl-(3-ethynylphenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 7
  • [ 62-53-3 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-phenyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 8
  • [ 108-42-9 ]
  • [ 162363-46-4 ]
  • (3-chloro-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 9
  • [ 626-01-7 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-(3-iodo-phenyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 10
  • [ 2237-30-1 ]
  • [ 162363-46-4 ]
  • 3-(6,7-diethoxy-quinazolin-4-ylamino)-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 11
  • [ 95-74-9 ]
  • [ 162363-46-4 ]
  • (3-chloro-4-methyl-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 12
  • [ 95-76-1 ]
  • [ 162363-46-4 ]
  • (3,4-dichloro-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Heating;
  • 14
  • [ 162363-46-4 ]
  • 4-[18F]fluoroaniline hydrochloride [ No CAS ]
  • 6,7-diethoxy-4-(4-[(18)F]fluoroanilino)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 85℃;
In N,N-dimethyl-formamide at 100℃; for 0.25h; 4.1.4. Synthesis of [18F]fluoroanilinoquinazolines General procedure: The dried [18F]fluoroaniline-hydrochlorides were coupled to 6,7-diethoxy- (2.2 mg, 9 μmol) or 6,7-dimethoxy-4-chloro-quinazoline (2.2 mg, 10 μmol) in 250 μL of DMF and reacted at 100 °C for 15 min. The reaction mixture was made basic with 1 N NaOH (1 mL) and loaded onto an activated C18 Sep-Pak cartridge. The cartridge was flushed with 4 mL of H2O, eluted with 2 mL of MeOH and filtered through Celite and a 0.45 mm nylon membrane filter prior to preparative HPLC purification.The reaction mixtures were purified by preparative HPLC purification (column; Beckman Ultrasphere ODS-5 μm, 10 mm × 25 cm, mobile phase; 65:35 (v/v) CH3OH: (1% Et3N in H2O adjusted to pH 7.4 with H3PO4), flow rate; 4 mL min-1 ([18F]1a-c), 6 mL min-1 ([18F]2a-c)). The column eluent was monitored for UV absorbance at 254 nm (UV detector: Linear, UV 106) and radioactivity (detector: Carroll and Ramsey Associates, Model 105S). All [18F]fluoroanilinoquinazolines were identified by HPLC via co-injection of an aliquot of the final product with authentic sample, prepared as previously described by our group.26 Compounds [18F]1a-c were isolated at a flow rate of 4.0 mL min-1 and had retention times of 7, 13 and 10.5 min, respectively. Compounds [18F]2a-c were isolated at a flow rate of 6 mL min-1 and had retention times of 9.5, 12 and 14.5 min, respectively. Compounds [18F]1 and [18F]2 had high radiochemical purities (>95%). Specific activities were determined by comparing the integration of the HPLC peak area to a standard curve generated by an authentic sample of the compound at various concentrations.
  • 15
  • [ 162363-46-4 ]
  • C6H6(18)FN*ClH [ No CAS ]
  • 6,7-diethoxy-4-(3-[(18)F]fluoroanilino)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 85℃;
In N,N-dimethyl-formamide at 100℃; for 0.25h; 4.1.4. Synthesis of [18F]fluoroanilinoquinazolines General procedure: The dried [18F]fluoroaniline-hydrochlorides were coupled to 6,7-diethoxy- (2.2 mg, 9 μmol) or 6,7-dimethoxy-4-chloro-quinazoline (2.2 mg, 10 μmol) in 250 μL of DMF and reacted at 100 °C for 15 min. The reaction mixture was made basic with 1 N NaOH (1 mL) and loaded onto an activated C18 Sep-Pak cartridge. The cartridge was flushed with 4 mL of H2O, eluted with 2 mL of MeOH and filtered through Celite and a 0.45 mm nylon membrane filter prior to preparative HPLC purification.The reaction mixtures were purified by preparative HPLC purification (column; Beckman Ultrasphere ODS-5 μm, 10 mm × 25 cm, mobile phase; 65:35 (v/v) CH3OH: (1% Et3N in H2O adjusted to pH 7.4 with H3PO4), flow rate; 4 mL min-1 ([18F]1a-c), 6 mL min-1 ([18F]2a-c)). The column eluent was monitored for UV absorbance at 254 nm (UV detector: Linear, UV 106) and radioactivity (detector: Carroll and Ramsey Associates, Model 105S). All [18F]fluoroanilinoquinazolines were identified by HPLC via co-injection of an aliquot of the final product with authentic sample, prepared as previously described by our group.26 Compounds [18F]1a-c were isolated at a flow rate of 4.0 mL min-1 and had retention times of 7, 13 and 10.5 min, respectively. Compounds [18F]2a-c were isolated at a flow rate of 6 mL min-1 and had retention times of 9.5, 12 and 14.5 min, respectively. Compounds [18F]1 and [18F]2 had high radiochemical purities (>95%). Specific activities were determined by comparing the integration of the HPLC peak area to a standard curve generated by an authentic sample of the compound at various concentrations.
  • 16
  • [ 162363-46-4 ]
  • 2-[18F]fluoroaniline hydrochloride [ No CAS ]
  • 6,7-diethoxy-4-(2-[(18)F]fluoroanilino)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 85℃;
In N,N-dimethyl-formamide at 100℃; for 0.25h; 4.1.4. Synthesis of [18F]fluoroanilinoquinazolines General procedure: The dried [18F]fluoroaniline-hydrochlorides were coupled to 6,7-diethoxy- (2.2 mg, 9 μmol) or 6,7-dimethoxy-4-chloro-quinazoline (2.2 mg, 10 μmol) in 250 μL of DMF and reacted at 100 °C for 15 min. The reaction mixture was made basic with 1 N NaOH (1 mL) and loaded onto an activated C18 Sep-Pak cartridge. The cartridge was flushed with 4 mL of H2O, eluted with 2 mL of MeOH and filtered through Celite and a 0.45 mm nylon membrane filter prior to preparative HPLC purification.The reaction mixtures were purified by preparative HPLC purification (column; Beckman Ultrasphere ODS-5 μm, 10 mm × 25 cm, mobile phase; 65:35 (v/v) CH3OH: (1% Et3N in H2O adjusted to pH 7.4 with H3PO4), flow rate; 4 mL min-1 ([18F]1a-c), 6 mL min-1 ([18F]2a-c)). The column eluent was monitored for UV absorbance at 254 nm (UV detector: Linear, UV 106) and radioactivity (detector: Carroll and Ramsey Associates, Model 105S). All [18F]fluoroanilinoquinazolines were identified by HPLC via co-injection of an aliquot of the final product with authentic sample, prepared as previously described by our group.26 Compounds [18F]1a-c were isolated at a flow rate of 4.0 mL min-1 and had retention times of 7, 13 and 10.5 min, respectively. Compounds [18F]2a-c were isolated at a flow rate of 6 mL min-1 and had retention times of 9.5, 12 and 14.5 min, respectively. Compounds [18F]1 and [18F]2 had high radiochemical purities (>95%). Specific activities were determined by comparing the integration of the HPLC peak area to a standard curve generated by an authentic sample of the compound at various concentrations.
  • 17
  • [ 162363-46-4 ]
  • C6H5Cl(18)FN*ClH [ No CAS ]
  • C18H17Cl(18)FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 85℃;
  • 18
  • [ 162363-46-4 ]
  • C6H5Br(18)FN*ClH [ No CAS ]
  • C18H17Br(18)FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 85℃;
  • 19
  • [ 57976-57-5 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-(3-pyridin-3-yl-phenyl)-amine [ No CAS ]
  • 25
  • [ 110-85-0 ]
  • [ 162363-46-4 ]
  • [ 205259-62-7 ]
YieldReaction ConditionsOperation in experiment
100% In isopropyl alcohol for 4h; Heating;
  • 26
  • [ 372-19-0 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-(3-fluoro-phenyl)-amine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In N,N-dimethyl-formamide at 80℃;
  • 27
  • [ 348-54-9 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-(2-fluoro-phenyl)-amine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In N,N-dimethyl-formamide at 80℃;
  • 28
  • [ 108-42-9 ]
  • [ 162363-46-4 ]
  • (3-chloro-phenyl)-(6,7-diethoxy-quinazolin-4-yl)-amine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In N,N-dimethyl-formamide at 80℃; for 0.666667h;
  • 29
  • [ 140-75-0 ]
  • [ 162363-46-4 ]
  • 4-[(4'-fluorobenzyl)amino]-6,7-diethoxyquinazoline hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In N,N-dimethyl-formamide at 80℃;
  • 30
  • [ 371-40-4 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-(4-fluoro-phenyl)-amine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In N,N-dimethyl-formamide at 80℃;
  • 31
  • [ 454-67-1 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-(3-fluoro-5-trifluoromethyl-phenyl)-amine; hydrochloride [ No CAS ]
  • 32
  • [ 1823-14-9 ]
  • [ 162363-46-4 ]
  • C23H26N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-phenyl-1-pentyne With Schwartz's reagent In tetrahydrofuran Stage #2: 4-Chloro-6,7-diethoxyquinazoline In tetrahydrofuran Further stages.;
  • 33
  • C19H15NSO2 [ No CAS ]
  • [ 162363-46-4 ]
  • C31H27N3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide
  • 34
  • [ 162363-46-4 ]
  • [ 32545-00-9 ]
  • C23H20N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide
  • 35
  • C11H7FN2 [ No CAS ]
  • [ 162363-46-4 ]
  • C23H19N4O2F [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide
  • 36
  • [ 221697-97-8 ]
  • [ 162363-46-4 ]
  • [ 221698-02-8 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide
  • 37
  • [ 16520-62-0 ]
  • [ 162363-46-4 ]
  • C22H24N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-Phenyl-1-butyne With Schwartz's reagent In tetrahydrofuran Stage #2: 4-Chloro-6,7-diethoxyquinazoline In tetrahydrofuran Further stages.;
  • 38
  • C19H25NO2 [ No CAS ]
  • [ 162363-46-4 ]
  • [ 958884-84-9 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine In N,N-dimethyl-formamide
  • 39
  • [ 536-74-3 ]
  • [ 162363-46-4 ]
  • C20H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: phenylacetylene With Schwartz's reagent In tetrahydrofuran Stage #2: 4-Chloro-6,7-diethoxyquinazoline In tetrahydrofuran Further stages.;
  • 40
  • [ 5409-31-4 ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 67 percent / HNO3; acetic acid / 2.08 h / 20 °C 2: 44 percent / SnCl2; aq. HCl / 2 h / 20 °C 3: 57 percent / 80 - 200 °C 4: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating
  • 41
  • [ 20197-71-1 ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 76 percent / aq. NaOH / 1 h / Heating 2: 57 percent / 80 - 200 °C 3: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating
  • 42
  • [ 20197-72-2 ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 57 percent / 80 - 200 °C 2: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating
  • 43
  • [ 103796-34-5 ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 44 percent / SnCl2; aq. HCl / 2 h / 20 °C 2: 57 percent / 80 - 200 °C 3: 73 percent / oxalyl chloride; DMF / 1,2-dichloro-ethane / 2.5 h / Heating
  • 44
  • [ 162363-46-4 ]
  • N-Benzyl-4-(6,7-diethoxy-4-quinazolinyl)-1-piperazinethiocarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / propan-2-ol / 4 h / Heating
  • 45
  • [ 162363-46-4 ]
  • 4-(6,7-Diethoxy-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / propan-2-ol / 4 h / Heating
  • 46
  • [ 75332-44-4 ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / glacial AcOH; conc. HNO3 / 3 h 2: 100 percent / H2 / 10percent Pd/C / ethanol / 25 °C / 2585.81 Torr 3: 90 percent / ammonium carbonate / 3 h / 170 °C 4: 88 percent / POCl3 / 2 h / Heating
  • 48
  • [ 162363-46-4 ]
  • (6,7-diethoxy-quinazolin-4-yl)-[3-(2-phenyl-thiazol-4-yl)-phenyl]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 87 percent / propan-2-ol / 1 h / Heating 2: 65 percent / Br2 in AcOH; HBr / 0.33 h / Heating 3: 73 percent / ethanol / 2 h / Heating
  • 50
  • [ 460750-26-9 ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 25 °C / 2585.81 Torr 2: 90 percent / ammonium carbonate / 3 h / 170 °C 3: 88 percent / POCl3 / 2 h / Heating
  • 51
  • [ 57976-57-5 ]
  • [ 162363-46-4 ]
  • [ 460750-67-8 ]
  • (6,7-Diethoxy-guinazolin-4-yl)-(3-pyridin-3-yl-phenyl)-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.068 g (88%) In isopropyl alcohol; Example 1b (6,7-Diethoxy-guinazolin-4-yl)-(3-pyridin-3-yl-phenyl)-amine hydrochloride. A solution of 0.042 g (0.25 mmol) of <strong>[57976-57-5]3-pyridin-3-yl-phenylamine</strong> in 0.80 mL of 2-propanol was heated at reflux and treated with 0.050 g (0.20 mmol) of 4-chloro-6,7-diethoxyquinazoline added in a single portion. The mixture was heated for 2 hours, then cooled and filtered. The precipitate was washed with ethyl acetate and dried to afford 0.068 g (88%) of (6,7-diethoxy-quinazolin-4-yl)-(3-pyridin-3-yl-phenyl)-amine hydrochloride as colorless crystals, mp 255-256 C. 1 H NMR (dmso-d6): delta8.94 (s, 1 H); 8.79 (s, 1 H); 8.61 (d, 1 H); 8.23 (s, 1 H); 8.15 (d, 1 H); 8.06 (s, 1 H); 7.74-7.53 (m, 4 H); 4.23 (overlapping q, 4 H); 1.42 (overlapping t, 6 H). MS (API): m/z 387 (M+H+). Analysis (C23H22N4O2·HCl): Calculated: C 65.32, H 5.48, N 13.25; Found: C 65.72, H 5.45, N 12.86.
  • 52
  • [ 99-03-6 ]
  • [ 162363-46-4 ]
  • [ 460750-56-5 ]
  • 1-[3-(6,7-Diethoxy-cluinazolin-4-ylamino)-phenyl]-ethanone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.19 g (87%) In isopropyl alcohol 2.a.A (6,7-Diethoxy-guinazolin-4-yl)-[3-(2-methylamino-thiazol-4-yl)-phenyl]-amine hydrobromide. Step A: 1-[3-(6,7-Diethoxy-cluinazolin-4-ylamino)-phenyl]-ethanone hydrochloride. A solution of 4.30 g (16.9 mmol) of 4-chloro-6,7-diethoxyquinazoline in 80 mL of 2-propanol was heated at reflux and treated with 2.51 g (18.6 mmol) of 3-aminoacetophenone added in a single portion. Heating was continued for 1 hour, after which the reaction mixture was allowed to cool. The precipitated product was filtered, washed with 2-propanol and dried to afford 5.19 g (87%) of 1-[3-(6,7-diethoxy-quinazolin-4-ylamino)-phenyl]-ethanone hydrochloride, mp 258-260° C. 1H NMR (dmso-d6): δ8.81 (s, 1 H); 8.18 (m, 2 H); 7.97 (d, 1 H); 7.88 (d, 1 H); 7.62 (t, 1 H); 7.27 (s, 1 H); 4.24 (overlapping q, 4 H); 2.59 (s, 3 H); 1.43 (overlapping t, 6 H). MS (API): m/z 352 (M+H+). Analysis (C20H21N3O3·HCl): Calculated: C 61.93, H 5.72, N 10.83; Found: C 62.07, H 5.78, N 10.86.
  • 53
  • [ 162363-46-4 ]
  • [ 460750-29-2 ]
  • [ 460750-55-4 ]
  • 4-[3-(6,7-Diethoxy-guinazolin-4-ylamino)-phenyl]-thiazole-2-carboxyic acid amide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.152 g (56%) In ethanol 1.a Example 1a Example 1a 4-[3-(6,7-Diethoxy-guinazolin-4-ylamino)-phenyl]-thiazole-2-carboxyic acid amide hydrochloride. A solution of 0.157 g (0.62 mmol) of 4-chloro-6,7-diethoxyquinazoline in 2.5 mL of ethanol was heated at reflux and treated with 0.136 g (0.62 mmol) of 4-(3-aminophenyl)-thiazole-2-carboxylic acid amide dissolved in 4 mL of ethanol added in a single portion. Heating was continued for 30 minutes, after which the reaction mixture was allowed to cool. The precipitated product was filtered, washed with ethanol and dried to afford 0.152 g (56%) of 4-[3-(6,7-diethoxy-quinazolin-4-ylamino)-phenyl]-thiazole-2-carboxylic acid amide hydrochloride, mp 264-266° C. 1H NMR (dmso-d6): δ11.40 (s, 1 H); 8.79 (s, 1 H); 8.42 (d, 1 H); 8.28 (s, 1 H); 8.24 (s, 1 H); 7.99 (d, 1 H); 7.93 (s, 1 H); 7.62 (m, 1 H); 7.55 (m, 1 H); 7.32 (m, 1 H); 4.23 (overlapping q, 4 H); 1.41 (overlapping t, 6 H). MS (API): m/z 436 (M+H+). Analysis (C22H21N5O3S·HCl): Calculated: C 55.99, H 4.70, N 14.84; Found: C 56.11, H 4.70, N 14.72.
  • 54
  • [ 162363-46-4 ]
  • [ 460750-31-6 ]
  • [ 460750-60-1 ]
  • 2-[3-(6,7-Diethoxy-guinazolin-4-ylamino)-phenyl]-thiazole-4-carboxylic acid amide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.077 g (88%) In ethanol 1.c Example 1c Example 1c 2-[3-(6,7-Diethoxy-guinazolin-4-ylamino)-phenyl]-thiazole-4-carboxylic acid amide hydrochloride. A solution of 0.055 g (0.25 mmol) of 2-(3-aminophenyl)-thiazole-4-carboxylic acid amide in 1 mL of ethanol was heated at reflux and treated with 0.050 g (0.2 mmol) of 4-chloro-6,7-diethoxyquinazoline. The mixture was heated at reflux for 1 hour, then the precipitate was filtered, washed with ethanol and dried to afford 0.077 g (88%) of 2-[3-(6,7-diethoxy-quinazolin-4-ylamino)-phenyl]-thiazole-4-carboxylic acid amide hydrochloride as white crystals, mp 284-286° C. 1H NMR (dmso-d6): δ8.86 (s, 1 H); 8.34 (m, 2 H); 8.29 (m, 1 H); 7.97 (d, 1 H); 7.90 (m, 2 H); 7.70 (br, 1 H); 7.64 (t, 1 H); 7.35 (s, 1 H); 4.27 (overlapping q, 4 H); 1.46 (overlapping t, 6 H). MS (API): m/z 436 (M+H+). Analysis (C22H21N5O3S·HCl): Calculated: C 55.99, H 4.70, N 14.84; Found: C 55.69, H 4.64, N 14.62.
  • 55
  • [ 162363-46-4 ]
  • [ 460750-34-9 ]
  • [ 460750-76-9 ]
YieldReaction ConditionsOperation in experiment
0.069 g (82%) In isopropyl alcohol 1.d Example 1d Example 1d (6,7-Diethoxy-quinazolin-4-yl)-[4-fluoro-3-(2-methyl-thiazol-4-yl)-phenyl]-amine hydrochloride. A solution of 0.052 g (0.25 mmol) of 4-fluoro-3-(2-methyl-thiazol-4-yl)-phenylamine in 0.8 mL of 2-propanol was heated at reflux and treated with 0.050 g (0.2 mmol) of 4-chloro-6,7-diethoxyquinazoline. The mixture was heated at reflux for 1 hour, then the precipitate was filtered, washed with 2-propanol and dried to afford 0.069 g (82%) of (6,7-diethoxy-quinazolin-4-yl)-[4-fluoro-3-(2-methyl-thiazol-4-yl)-phenyl]-amine hydrochloride as white crystals, mp 280-281° C. 1 H NMR (dmso-d6): δ8.80 (s, 1 H); 8.30 (m, 1 H); 8.21 (s, 1 H); 7.88 (s, 1 H); 7.75 (m, 1 H); 7.43 (t, 1 H); 7.32 (s, 1 H); 4.25 (overlapping q, 4 H); 2.69 (s, 3 H); 1.42 (overlapping t, 6 H). MS (API): m/z 436 (M+H+). Analysis (C22H2,FN4O2S·HCl): Calculated: C 57.32, H 4.81, N 12.15; Found: C 57.62, H 4.79, N 12.14.
  • 56
  • [ 179246-15-2 ]
  • 4-Chloro-6,7-diethoxyguinazoline [ No CAS ]
  • [ 162363-46-4 ]
YieldReaction ConditionsOperation in experiment
8.02 g (88%) With sodium carbonate In water; ethyl acetate; trichlorophosphate 1.a Preparation 1a Preparation 1a 4-Chloro-6,7-diethoxyguinazoline. A solution of 8.45 g of 6,7-diethoxy-3H-quinazolin-4-one in 50 mL of phosphorus oxychloride was heated at reflux for 2 hours. The mixture was then cooled and concentrated. The residue was added to a solution of 120 g of sodium carbonate in 300 mL of water and 300 mL of ethyl acetate. The mixture was stirred for 15 minutes, then the ethyl acetate was washed with brine, dried, and concentrated. The residue was crystallized from 1-chlorobutane to give 8.02 g (88%) of 4-chloro-6,7-diethoxyquinazoline, mp 141-143° C. 1H NMR (CDCl3): δ8.83 (s, 1 H); 7.36 (s, 1 H); 7.30 (s, 1 H); 4.27 (overlapping q, 4 H); 1.56 (overlapping t, 6 H). MS (API): m/z 253, 255 (M+H+, chlorine isotope pattern).
YieldReaction ConditionsOperation in experiment
98%
  • 58
  • [ 183322-26-1 ]
  • [ 162363-46-4 ]
  • (6,7-diethoxyquinazolin-4-yl)-(3-(2’-trimethylsilylethynyl)-2-methylphenyl)amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In <i>tert</i>-butyl alcohol for 16h; Reflux; int-43 (6,7-Diethoxy-quinazolin-4-yl)-(3-ethynyl-2-methyl-phenyl)-amine hydrochloride 4-Chloro-6,7-diethoxyquinazoline (200 mg, 0.792 mmol) and 3-(2’-trimethylsilylethynyl-2-methyl-aniline (168mg, 0.871 mmol) in 4 mL of tert-butyl alcohol was refluxed for 16 hours. The cooled reaction mixture was diluted with 5mL of ethyl ether and filtered to afford solid (6,7-diethoxy-quinazolin-4-yl)-(3-(2’-trimethylsilyl-ethynyl)-2-methyl-phenyl)-amine hydrochloride which was washed with 10 mL of ethyl ether and dried in vacuo at 70°C. This material wasdesilated directly by treatment with 2 mL of methanol containing 1 drop of water and 100 mg of potassium carbonatefor 0.5 hours. The heterogeneous reaction mixture was filtered through Celite and vacuum evaporated to a residue whichwas dissolved in excess 1 N HCl in methanol, precipitated with ethyl ether, filtered and dried in vacuo at 70°C to affordthe title product; 160 mg (75%); mp 258-259.5°C.
  • 59
  • [ 162363-46-4 ]
  • C26H25BrFN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere
  • 60
  • [ 162363-46-4 ]
  • C26H27BFN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 3 h / 20 °C / Inert atmosphere 3.3: 1 h / pH 2 / Inert atmosphere
  • 61
  • [ 626-40-4 ]
  • [ 162363-46-4 ]
  • C18H17Br2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In 5,5-dimethyl-1,3-cyclohexadiene for 5h; Inert atmosphere; Reflux; 1.1 Step 1. Synthesis of Intermediate IV-1 Compound II (2.52 g, 10 mmol), compound III (2.51 g, 10 mmol) and diisopropylethylamine (DIPEA,3.88 g, 30 mmol) was dissolved in 50 mL of dry xylene and refluxed under nitrogen atmosphere until the reaction was completeUsually 5 hours). The reaction mixture was carefully poured into 200 mL of ice water, stirred, extracted with 50 mL of X3CH2C12, the combined phases were combined,Washed successively with 1% dilute hydrochloric acid (200 mL) and brine (100 mL), and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtrationEvaporated on a rotary evaporator to give compound IV, a white solid.
With N-ethyl-N,N-diisopropylamine In 5,5-dimethyl-1,3-cyclohexadiene for 5h; Inert atmosphere; 1.1 Step 1. Synthesis of Intermediate IV-1 Compound II (2.52 g, 10 mmol),Compound III (2.51 g, 10 mmol) and diisopropylethylamine (DIPEA, 3.88 g, 30 mmol)Dissolved in 50 mL of dry xylene,And then under the protection of nitrogen temperature rise,Until the reaction is complete (usually 5 hours).The reaction mixture was carefully poured into 200 mL of ice water,Stir,Extracted with 50 mL x 3 CH2Cl2,Combined extraction phase,Washed sequentially with 1% dilute hydrochloric acid (200 mL) and brine (100 mL)Dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration,The filtrate was evaporated to dryness on a rotary evaporator,To give compound IV,White solid
  • 62
  • [ 162363-46-4 ]
  • C26H29BN4O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 3 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: 3 h / 20 °C
  • 63
  • [ 162363-46-4 ]
  • C26H27BrN4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: 3 h / 20 °C
  • 64
  • [ 162363-46-4 ]
  • [ 218301-22-5 ]
  • C25H23FN4O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 13 h / Cooling with ice; Reflux
  • 65
  • [ 162363-46-4 ]
  • [ 218301-22-5 ]
  • C20H18FN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-Chloro-6,7-diethoxyquinazoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-fluoro-5-formylbenzonitrile In tetrahydrofuran; hexane at 20℃; for 3h; Inert atmosphere; 1.1 Step 1. Synthesis of Compound IV-1 Compound II-1 (2.53 g, 10 mmol) was dissolved in 25 mL of dry THF, stirred under nitrogen and cooled to -78 ° C with liquid nitrogen-ethanol. A 1.6 M n-BuLi solution in n-hexane (6.25 mL). After the addition was complete, the reaction mixture was stirred at this temperature for a further 1 h,Then a solution of III-1 (1.49 g, 10 mmol) dissolved in 3 mL of dry THF was slowly added dropwise using a syringe.After the addition was completed, the reaction mixture was stirred for a further 3 hours at room temperature,TLC showed the reaction was completed. The reaction mixture was carefully poured into 200 mL ice water, stirred and extracted with 50 mL × 3 CH 2 Cl 2. The combined extracts were washed with brine (100 mL) and dried over anhydrous sodium sulfate. The desiccant was filtered off with suction and the filtrate was evaporated to dryness on a rotary evaporator to give compound IV-1 as a white solid
  • 66
  • [ 42564-51-2 ]
  • [ 162363-46-4 ]
  • C24H23FN4O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / Cooling with ice 2.2: 12 h / Reflux
  • 67
  • [ 42564-51-2 ]
  • [ 162363-46-4 ]
  • C19H18FN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-Chloro-6,7-diethoxyquinazoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4-fluoro-3-nitrobenzaldehyde In tetrahydrofuran; hexane at 20℃; for 3h; Inert atmosphere; 1.1 Step 1. Synthesis of Compound IV-1 Compound II-1 (2.53 g, 10 mmol) was dissolved in 25 mL of dry THF, stirred under nitrogen and cooled to -78 ° C with liquid nitrogen-ethanol. A 1.6 M n-BuLi solution in n-hexane (6.25 mL). After the addition was complete, the reaction mixture was stirred at this temperature for a further 1 h,Then a solution of III-1 (1.69 g, 10 mmol) dissolved in 3 mL of dry THF was slowly added dropwise using a syringe.After the addition was completed, the reaction mixture was stirred for a further 3 hours at room temperature and TLC showed the reaction was complete. The reaction mixture was carefully poured into 200 mL ice water, stirred and extracted with 50 mL × 3 CH 2 Cl 2. The combined extracts were washed with brine (100 mL) and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration and the filtrate was evaporated to dryness on a rotary evaporator to give compound IV-1 as an off-white solid
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