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Chemical Structure| 193001-59-1 Chemical Structure| 193001-59-1

Structure of 193001-59-1

Chemical Structure| 193001-59-1

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Product Details of [ 193001-59-1 ]

CAS No. :193001-59-1
Formula : C15H11ClFN3O2
M.W : 319.72
SMILES Code : OC1=CC2=NC=NC(NC3=CC=C(Cl)C=C3F)=C2C=C1OC

Safety of [ 193001-59-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 193001-59-1 ]

* 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 [ 193001-59-1 ]

[ 193001-59-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 57616-74-7 ]
  • [ 193001-59-1 ]
  • 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-morpholinopropoxy)quinazoline [ No CAS ]
  • 2
  • [ 5344-27-4 ]
  • [ 193001-59-1 ]
  • 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(pyridin-4-yl)ethoxy)quinazoline hydrochloride [ No CAS ]
  • 3
  • [ 7583-53-1 ]
  • ethereal hydrogen chloride [ No CAS ]
  • [ 10465-81-3 ]
  • [ 193001-59-1 ]
  • [ 205193-45-9 ]
YieldReaction ConditionsOperation in experiment
33% With tributylphosphine; In dichloromethane; acetone; Alternatively the racemate may be made as follows: 1,1'-(Azodicarbonyl)dipiperidine (560 mg, 2.2 mmol) was added in portions to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (240 mg, 0.75 mmol), (prepared as described for the starting material in Example 2), 1-methyl-3-piperidinemethanol (115 mg, 0.89 mmol) and tributylphosphine (440 mg, 2.2 mmol) in methylene chloride (10 ml). The mixture was stirred for 18 hours, diluted with ether and the resulting precipitate was removed by filtration. The volatiles were removed from the filtrate by evaporation, and the residue was dissolved in acetone and ethereal hydrogen chloride (1.5 ml of a 1M solution, 1.5 mmol) was added. The precipitated product was collected by filtration and purified by column chromatography eluding with methylene chloride/methanol/aqueous ammonia (75/8/1). The purified solid product was triturated with ether collected by filtration and dried to give 4-(4chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-3-ylmethoxy)quinazoline (105 mg, 33percent). m.p. 211-212° C.; 1H NMR Spectrum: (DMSOd6) 1.08(m, 1H); 1.50(m, 1H); 1.78(m, 4H); 2.08(m, 1H); 2.16(m, 3H); 2.62(m, 1H); 2.82(m, 1H); 3.95(s, 3H); 4.00(d, 2H); 7.18(s, 1H); 7.32(m, 1H); 7.52(dd, 1H); 7.58(t, 1H); 7.79(s, 1H); 8.35(s, 1H); 9.52(s, 1H); MS-ESI: 431 [MH]+; Elemental analysis: Found C, 59.9; H, 5.5; N, 12.9; C22H24N4O2ClF 0.5H2O Requires C, 60.0; H, 5.7; N, 12.7percent.
  • 4
  • [ 5344-27-4 ]
  • [ 193001-59-1 ]
  • [ 1972-28-7 ]
  • 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(pyridin-4-yl)ethoxy)quinazoline hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With hydrogenchloride; triphenylphosphine; In methanol; dichloromethane; isopropyl alcohol; Example 37 Diethyl azodicarboxylate (315 mul, 2 mmol) was added dropwise to a solution of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (319.5 mg, 1 mmol), (prepared as described for the starting material in Example 24), triphenylphosphine (524 mg, 2 mmol) and 2-(4-pyridyl)ethanol (160 mg, 1.25 mmol), (Zhur. Obshchei. Khim. 1958, 28, 103-110), in methylene chloride (7 ml). The mixture was stirred for 1 hour at ambient temperature and the solvent was removed by evaporation. The residue was triturated with ether, the solid collected by filtration and purified by column chromatography eluding with methylene chloride/acetonitrile/methanol (85/10/5). The purified solid product was dissolved in a mixture of methylene chloride (50 ml) and methanol (50 ml) and 5M hydrochloric acid in isopropanol (0.5 ml) was added. After diluting with isopropanol (20 ml), the mixture was concentrated by evaporation. The precipitated solid was collected by filtration and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(4-pyridyl)ethoxy)quinazoline hydrochloride (125 mg, 25%). m.p. 189-191 C. 1 H NMR Spectrum: (DMSOd6; CF3 COOD) 3.55(t, 2H); 3.99(s, 3H); 4.64(t, 2H); 7.46(s, 1H); 7.48(d, 1H); 7.62(t, 1H); 7.67(dd, 1H); 8.16(d, 2H); 8.17(s, 1H); 8.88(s, 1H); 8.94(d, 1H) MS - ESI: 425 [MH]+ Elemental Analysis: Found C 52.0 H 4.3 N 11.1 C22 H18N4 O2 ClF 0.5H2 O 1.95HCl Requires C 52.3 H 4.2 N 11.1%
 

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