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[ CAS No. 16499-62-0 ] {[proInfo.proName]}

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Chemical Structure| 16499-62-0
Chemical Structure| 16499-62-0
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Product Details of [ 16499-62-0 ]

CAS No. :16499-62-0 MDL No. :MFCD08236729
Formula : C8H4ClFN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :JHBYQJRHJVEKPK-UHFFFAOYSA-N
M.W : 182.58 Pubchem ID :16227013
Synonyms :

Safety of [ 16499-62-0 ]

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

Application In Synthesis of [ 16499-62-0 ]

* 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 [ 16499-62-0 ]

[ 16499-62-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 16499-57-3 ]
  • [ 16499-62-0 ]
YieldReaction ConditionsOperation in experiment
~ 100% With thionyl chloride;Heating / reflux; 7-Fluoro-3H-quinazolin-4-one (8.2 g, 50 mmol) is heated at reflux in thionyl chloride (80 mL). Concentration affords the expected 4-Chloro-7-fluoro-quinazoline (9.1 g, quant).
With thionyl chloride; N,N-dimethyl-formamide; for 8h;Reflux; General procedure: A mixture of 4-quinazolone analogues 2a-2j (8.0 mmol) in SOCI2 (27.4 mL) containing DMF (2 drops) was refluxed for 8 h. SOCI2 was removed under reduced pressure and the residue was dissolved in DCM. The solution was washed with saturated NaHCO3 solution and brine, respectively, dried over anhydrous Na2S04 and then concentrated under reduced pressure to yield the compounds 3a-3j (65.1-88.9percent yield) as white or off-white solid.
  • 2
  • [ 16499-62-0 ]
  • [ 591-19-5 ]
  • [ 198961-95-4 ]
  • 3
  • [ 16499-62-0 ]
  • [ 130339-51-4 ]
  • [1-(4-difluoromethoxy-phenyl)-propyl]-(7-fluoro-quinazolin-4-yl)-amine [ No CAS ]
  • 5
  • [ 16499-62-0 ]
  • [ 765-30-0 ]
  • Cyclopropyl-(7-fluoro-quinazolin-4-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In dichloromethane; at 20℃; 4-Chloro-7-fluoro-quinazoline (0.73 g, 4 mmol) and cyclopropylamine (0.23 g, 4 mmol) are stirred in dichloromethane at ambient temperature overnight. The solid product is precipitated with hexanes, filtered, and washed with hexane and ethyl acetate, affording 0.3 g of desired Cyclopropyl-(7-fluoro-quinazolin-4-yl)-amine. The filtrate is concentrated and precipitated with hexanes, yielding an additional 0.35, for a combined yield of 80%. LC/MS m/z=204 [M+H]+).
  • 6
  • [ 16499-62-0 ]
  • N4-(3-Bromo-phenyl)-N7-methyl-quinazoline-4,7-diamine [ No CAS ]
  • 7
  • [ 16499-62-0 ]
  • N4-(3-Bromo-phenyl)-N7-ethyl-quinazoline-4,7-diamine [ No CAS ]
  • 8
  • [ 16499-62-0 ]
  • N4-(3-Bromo-phenyl)-N7,N7-dimethyl-quinazoline-4,7-diamine [ No CAS ]
  • 9
  • [ 99724-19-3 ]
  • [ 16499-62-0 ]
  • [1-(7-fluoro-quinazolin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 - 100℃; for 0.375h; A vial was charged with 4-chloro-7-fluoro-quinazoline (2.00 g, 11.0 mmol) (WO 9609294 A1), pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.05 g, 11.0 mmol), DMSO (2.64 mL), and DIPEA (2.10 mL, 12.0 mmol) in quick succession. The mixture was stirred at "rt" for 20 min, during which time the reaction spontaneously warmed and became a homogeneous reddish-brown solution. The reaction was then stirred at 100 C. for 2.5 min to ensure complete reaction. The solution was shaken with water (20 mL) to dissolve the DMSO into the aqueous phase, and was extracted with EtOAc (1*20 mL). The organic layer was washed with 4 M NaCl (1*20 mL) and dried (Na2SO4). Upon addition of Na2SO4 to the organic phase, the title compound began to precipitate out. This was collected by filtration (easily decanted from the wet drying agent), dried, and powdered to afford the title compound as an off-white powder (1.42 g, 39%).
39% With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 - 100℃; for 0.375h; EXAMPLE NO. 70; 1-(4-Isopropyl-phenyl)-3-(1-{7-[2-(2-oxo-pyrrolidin-1-yl)-ethoxy]-quinazolin-4-yl}-pyrrolidin-3-yl)-urea (Compound No. 70); a. [1-(7-Fluoro-quinazolin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester; A vial was charged with 4-chloro-7-fluoro-quinazoline (2.00 g, 11.0 mmol) (WO 9609294 A1), pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.05 g, 11.0 mmol), DMSO (2.64 mL), and DIPEA (2.10 mL, 12.0 mmol) in quick succession. The mixture was stirred at “rt” for 20 min, during which time the reaction spontaneously warmed and became a homogeneous reddish-brown solution. The reaction was then stirred at 100 C. for 2.5 min to ensure complete reaction. The solution was shaken with water (20 mL) to dissolve the DMSO into the aqueous phase, and was extracted with EtOAc (1×20 mL). The organic layer was washed with 4 M NaCl (1×20 mL) and dried (Na2SO4). Upon addition of Na2SO4 to the organic phase, the title compound began to precipitate out. This was collected by filtration (easily decanted from the wet drying agent), dried, and powdered to afford the title compound as an off-white powder (1.42 g, 39%).
  • 10
  • [ 124443-68-1 ]
  • [ 16499-62-0 ]
  • [ 916731-79-8 ]
YieldReaction ConditionsOperation in experiment
100% With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20℃; for 2.61667 - 2.63333h; EXAMPLE 65; 4-[7-(3-Methanesulfonylamino-propoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-isopropoxy-phenyl)-amide; a. 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester; A mixture of 4-chloro-7-fluoro-quinazoline (2.87 g, 15.4 mmol) (WO 9609294 A1) and piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (4.15 g, 17.1 mmol), as prepared in Example 1b, was placed in a -78 C. bath for 5 min under argon before adding a 1.08 M LiHMDS/THF solution (17.8 mL, 19.2 mmol) rapidly by syringe along the sides of the flask (to allow cooling and dispersion of the hindered base before reaction with the ester). Following completion of LiHMDS/THF addition, the reaction was manually swirled in the -78 C. bath for 2-3 min before removing the cold bath and allowing the mixture to stir with gradual warming to rt. After 2.5 h stirring at rt, the dark brown homogeneous solution was quenched with 1.0 M NaH2PO4 (38 mL) and extracted with DCM (1×150 mL and 1×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure, and subject to high vacuum at 90 C. with toluene chasers (3×10 mL) to provide the crude title compound as an opaque thick yellow oil that was used in the next step without further purification (6.83 g, “114%” crude yield). 1H-NMR (300 MHz, CDCl3) δ 9.26 (s, 1H), 8.11 (dd, 1H), 7.70 (dd, 1H), 7.36 (ddd, 1H), 3.74-3.64 (m, 2H), 3.62-3.51 (m, 2H), 3.61 (s, 3H), 2.47-2.38 (br m, 4H), 1.46 (s, 9H). LC/MS (ESI): calcd mass 389.2, found 390.1 (MH)+.
  • 11
  • [ 1206694-33-8 ]
  • [ 16499-62-0 ]
  • [ 1206694-07-6 ]
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