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Chemical Structure| 52791-05-6
Chemical Structure| 52791-05-6
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Product Details of [ 52791-05-6 ]

CAS No. :52791-05-6 MDL No. :MFCD09838958
Formula : C10H7ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :222.63 Pubchem ID :-
Synonyms :

Safety of [ 52791-05-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52791-05-6 ]

* 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 [ 52791-05-6 ]

[ 52791-05-6 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 52537-00-5 ]
  • [ 52791-05-6 ]
  • 4-(6-Chloro-2,3-dihydro-indol-1-yl)-7,8-dihydro-[1,4]dioxino[2,3-g]guinazoline [ No CAS ]
  • [ 172078-20-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In isopropyl alcohol; acetone; Example 1 4-(6-Chloro-2,3-dihydro-indol-1-yl)-7,8-dihydro-[1,4]dioxino[2,3-g]guinazoline To <strong>[52537-00-5]6-chloroindoline</strong> (52 mg, 0.339 mmol) and pyridine (23.3 mg, 0.294 mmol) in i-PrOH (3 mL) was added 4-chloro-6,7-(ethylenedioxy)quinazoline (65 mg, 0.284 mmol). The mixture was heated to reflux under dry N2(g) for 16 hours and then concentrated in vacuo. The residue was partitioned between CHCl3 and saturated aqueous NaHCO3, and the organic phase was washed with brine, dried over Na2 SO4(s), and concentrated in vacuo. The residue was flash chromatographed on silica using 30% acetone/hexanes to afford 84 mg of 4-(6-chloro-2,3-dihydro-indol-1-yl)-7,8-dihydro-[1,4]dioxino [2,3-g]quinazoline as its free-base (M.P. 209-211 C.; GC/MS: 339 (M+); anal. RP18-HPLC RT: 5.02 min).
  • 2
  • [ 37045-73-1 ]
  • [ 52791-05-6 ]
  • [ 1456819-61-6 ]
YieldReaction ConditionsOperation in experiment
82% In isopropyl alcohol; at 80℃; for 0.25h;Microwave irradiation; General procedure: A mixture of 4-chloroquinazoline (23a-c,[1] 23d-f, 31-33[3]) (0.5 mmol) and the appropriate aniline (0.5 mmol) in i-PrOH (1 mL) was microwave irradiated at 80 C (power set point 60 W; ramp time1 min; hold time 15 min). After cooling, the obtained precipitate was collected by filtration to give compounds 5-18 and 33-35 as hydrochlorides.
  • 3
  • [ 2243-47-2 ]
  • [ 52791-05-6 ]
  • [ 1401243-69-3 ]
YieldReaction ConditionsOperation in experiment
88% In isopropyl alcohol at 80℃; for 0.25h; Microwave irradiation; General procedure for 4-anilinoquinazolines 5-18, 34-36 General procedure: A mixture of 4-chloroquinazoline (23a-c,[1] 23d-f, 31-33[3]) (0.5 mmol) and the appropriate aniline (0.5 mmol) in i-PrOH (1 mL) was microwave irradiated at 80 °C (power set point 60 W; ramp time1 min; hold time 15 min). After cooling, the obtained precipitate was collected by filtration to give compounds 5-18 and 33-35 as hydrochlorides.
  • 4
  • [ 15889-32-4 ]
  • [ 52791-05-6 ]
  • (7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)-[3'-(pyridinyl-2''-yl)phenyl]amine hydrochloride [ No CAS ]
  • 5
  • [ 2305-87-5 ]
  • [ 52791-05-6 ]
  • (7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)-(4'-phenylpyrimidin-2''-yl)amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% Stage #1: 4-phenylpyrimidin-2-amine With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 4-chloro-7,8-dihydro[1,4]-dioxino[2,3-g]quinazoline In tetrahydrofuran at 80℃; for 0.25h; Microwave irradiation;
  • 6
  • [ 1145671-36-8 ]
  • [ 107-04-0 ]
  • [ 52791-05-6 ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 8h;
67% With potassium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere; Heating; 1 [Cyclization] To a solution of diol 2 (530 mg, 2.6959 mmol) in DMF (13.5 mL, 0.2 M) was added in one portion potassium carbonate (1490 mg), followed by successive dropwise addition of 1 -bromo-2-chloroethane (1.3 mL) at room temperature under Ar. After being heated at 60 °C (bath temperature) with stirring for 24 h, the reaction mixture was cooled to room temperature, quenched with H2O (50 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed successively with H2O and saturated brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexanes/EtOAc, 6/1 to 3/1) to give fused-chloroquinazoline 3 (404 mg, 67%); NMR (400 MHz, CDCh) δ 8.84 (s, 1H), 7.64 (s, 1H), 7.47 (s, 1H), 4.43-4.45 (m, 2 H), 4.39-4.42 (m, 2 H). [known compound; Chilin, A. et al. J. Med. Chem. 2010, 53, 1862-1866]
67% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; 1 [Cyclization] To a solution of diol 2 (530 mg, 2.6959 mmol) in DMF (13.5 niL, 0.2 M) was added in one portion potassium carbonate (1490 mg), followed by successive dropwise addition of l-bromo-2-chloroethane (1.3 mL) at room temperature under Ar. After being heated at 60 °C (bath temperature) with stirring for 24 h, the reaction mixture was cooled to room temperature, quenched with 0 (50 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed successively with H2O and saturated brine, dried over anhydrous MgSOr, filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexanes/EtOAc, 6/1 to 3/1) to give fused-chloroquinazoline 3 (404 mg, 67%); NMR (400 MHz, CDCI3) d 8.84 (s, 1 H), 7.64 (s, 1 H), 7.47 (s, 1 H), 4.43-4.45 (m, 2 H), 4.39-4.42 (m, 2 H). [known compound; Chiiin, A. et ai J. Med. i 'hem. 2010, 55, 1862-1866]
41% With potassium carbonate In N,N-dimethyl-formamide at 23 - 70℃; for 16h;

  • 7
  • [ 2106-04-9 ]
  • [ 52791-05-6 ]
  • N-(3-chloro-2-fluorophenyl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 3-chloro-2-fluoroaniline; 4-chloro-7,8-dihydro[1,4]-dioxino[2,3-g]quinazoline In isopropyl alcohol at 80℃; Microwave irradiation; Stage #2: With sodium hydrogencarbonate In water
82% In N,N-dimethyl-formamide for 24h; Inert atmosphere; Heating; 1 [JGK010] To a solution of fused-chloroquinazoline 3 (114 mg, 0.5120 mmol) in DMF (2.6 mL) was dropwise added 3-chloro-2-fluoroaniline (0.10 mL) at room temperature. After being heated at 60 °C (bath temperature) with stirring for 24 h, the reaction mixture was cooled to room temperature and diluted with Et20 (30.0 mL) to give white suspension. The resulting white solid were washed successively with Et20 (2 χ 50 mL) and collected to give JGK010 (140 mg, 82%); NMR (400 MHz, CDCh) δ 8.68 (s, 1H), 8.59 (ddd, J= 3.2, 6.8, 6.8 Hz, 1H), 7.39 (s, 1H), 7.34 (s, 1H), 7.29 (s, 1H), 7.10-7.18 (m, 2 H), 4.38-4.43 (m, 4 H); NMR (500 MHz, OMSO-d6) δ 11.78 (s, 1H), 8.79 (s, 1H), 8.45 (s, 1H), 7.62 (t, J = 7.0 Hz, 1H), 7.50 (t, J= 7.0 Hz, 1H), 7.43 (s, 1H), 7.34 (t, J= 8.0 Hz, 1H), 4.46-4.53 (m, 2 H), 4.40-4.52 (m, 2 H) ; 13C NMR (125 MHz, OMSO-de) δ 159.8, 154.0, 152.2, 149.9, 145.7, 135.2, 129.9, 128.1, 126.4, 125.8, 120.9, 111.3, 108.1, 105.8, 65.5, 64.6; HRMS-ESI [M+H]+ found 332.0551 [calcd for C16H11CIFN3O2 331.0518].
82% In N,N-dimethyl-formamide at 60℃; for 24h; 1 [JGK010] To a solution of fused-chloroquinazoline 3 (114 mg, 0.5120 mmol) in DMF (2.6 ml,) was dropwise added 3-chloro-2-fluoroanillne (0.10 ml,) at room temperature. After being heated at 60 °C (bath temperature) with stirring for 24 h, the reaction mixture was cooled to room temperature and diluted with Et Q (30.0 mL) to give white suspension. The resulting white solid were washed successively with Et?Q (2 c 50 mL) and collected to give JGK010 (140 mg, 82%); NMR (400 MHz, CDC33) d 8 68 (s, I H), 8.59 (ddd, J = 3.2, 6 8, 6 8 Hz, 1 H), 7.39 (s, 1 H), 7 34 (s, I H), 7.29 (s, 1 H), 7. 10-7 18 (m, 2 H), 4.38-4.43 (m, 4 H); 4 1 NMR (500 MHz, DMSO-iA) 6 11.78 (s, 1 H), 8.79 (s, 1 H), 8.45 (s, 1 H), 7.62 (t, ./ = 7.0 Hz, 1 H), 7.50 (t, J= 7.0 Hz, 1 H), 7.43 (s, 1 H), 7.34 (t, J= 8.0 Hz, 1 H), 4.46-4.53 (m, 2 H), 4.40-4.52 (m, 2 H) ; 13C NMR (125 MHz, DMSO-i) d 159.8, 154.0, 152/2, 149.9, 145.7, 135.2, 129 9, 128.1, 126.4, 125.8, 120.9, 1 1 1.3, 108.1, 105.8, 65.5, 64 6; HRMS-ESI [ M H | found 332.055 1 [ealed for C16H11CIFN3O2 331 .0518]
  • 8
  • [ 65615-90-9 ]
  • [ 52791-05-6 ]
  • C25H28N4O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In N,N-dimethyl-formamide for 12h; Inert atmosphere; Heating; 1 Preparation of JGK015 To a solution of L-amino acid analogue A (227 mg, 0.7712 mmol) in DMF (3.0 mL) was added in one portion fused-chloroquinazoline 3 (117 mg, 0.5932 mmol) at room temperature. After being heated at 35 °C (bath temperature) with stirring for 12 h, the reaction mixture was cooled to room temperature and diluted with saturated brine (30.0 mL) and EtOAc (30.0 mL) to give yellow suspension. The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 50 mL). The combined organic layers were concentrated in vacuo. The residue was purified by column chromatography (silica gel, CEkCh/MeOH, 40/1 to 10/1) to give JGK015 (261 mg, 92%); NMR (500 MHz, CDCh) δ 8.57 (s, 1H), 7.64 (s, 1H), 7.61 (d, J= 8.0 Hz, 2 H), 7.37 (s, 1H), 7.27 (s, 1H), 7.08 (d, J= 8.5 Hz, 2 H), 5.09 (d, J= 7.5 Hz, 1H), 4.54 (dd, J = 6.0, 13.5 Hz, 1H), 4.31-4.33 (m, 2 H), 4.27-4.29 (m, 2 H), 3.68 (s, 3 H), 3.06 (dd, J= 5.6, 14.0 Hz, 1H), 3.00 (dd, J= 6.1, 13.8 Hz, 1H), 1.39 (s, 9 H); 13C NMR (125 MHz, CDCh) 6 172.4, 156.5, 155.2, 153.6, 149.1, 146.3, 143.8, 137.6, 131.6, 129.7, 121.7, 113.8, 110.3, 106.6, 80.0, 64.4, 64.2, 54.4, 52.2, 37.6, 28.3; HRMS-ESI [M+H]+ found 481.2082 [calcd for C25H28N4O6 480.2003].
92% In N,N-dimethyl-formamide at 35℃; for 12h; 1 Preparation of JGK015 To a solution of L-amino acid analogue A (227 mg, 0.7712 mmol) in DMF (3.0 niL) was added In one portion fused-chioroquinazoiine 3 (1 17 mg, 0.5932 mmol) at room temperature. After being heated at 35 °C (bath temperature) with stirring for 12 h, the reaction mixture was cooled to room temperature and diluted with saturated brine (30.0 niL) and EtOAc (30.0 ml.) to give yellow suspension. The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 50 mL). The combined organic layers were concentrated in vacuo. The residue was purified by column chromatography (silica gel, Cl bCh/MeOi f 40/1 to 10/1) to give J GKO 15 (261 mg, 92%); NMR (500 MHz, CDCh) d 8.57 (s, 1 H), 7.64 (s, 1 H), 7.61 (d, J ---- 8.0 Hz, 2 H), 7.37 (s, 1 H), 7.27 (s, 1 H), 7.08 (d, J ---- 8.5 Hz, 2 H), 5.09 (d, J ------ 7.5 Hz, 1 H), 4.54 (dd, J= 6.0, 13.5 Hz, 1 H), 4.31-4.33 (m, 2. H), 4.27-4.29 (m, 2. H), 3.68 (s, 3 H), 3.06 (dd, J ------ 5.6, 14.0 Hz, 1 H), 3.00 (dd, J ------ 6.1, 13.8 Hz, 1 H), 1.39 (s, 9 H); i3C NMR (125 MHz, CDCh) d 172.4, 156.5, 155.2, 153.6, 149.1, 146.3, 143.8, 137.6, 131.6, 129.7, 12 1 .7. 1 13.8, 110.3, 106.6, 80.0, 64.4, 64.2, 54.4, 52.2, 37.6, 28.3; HRMS-ESI j M H j found 481.2082 j calcd for (' -d IwN iCL 480.2003].
  • 9
  • [ 2924-09-6 ]
  • [ 52791-05-6 ]
  • N-(5-bromo-2-fluorophenyl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With hydrogenchloride In 1,4-dioxane; acetonitrile at 80℃; for 0.5h; Microwave irradiation;
  • 10
  • [ 1262198-07-1 ]
  • [ 52791-05-6 ]
  • N-(3-bromo-2,6-difluorophenyl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-amine [ No CAS ]
  • 11
  • [ 363-81-5 ]
  • [ 52791-05-6 ]
  • N-(2,4,6-trifluorophenyl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2,4,6-trifluoroaniline; 4-chloro-7,8-dihydro[1,4]-dioxino[2,3-g]quinazoline With hydrogenchloride In 1,4-dioxane; acetonitrile at 80℃; for 0.5h; Microwave irradiation; Stage #2: With sodium hydrogencarbonate In water
  • 12
  • [ 1269232-95-2 ]
  • [ 52791-05-6 ]
  • N-(3-bromo-5-chloro-2-fluorophenyl)-7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With hydrogenchloride In 1,4-dioxane; acetonitrile at 80℃; for 0.5h; Microwave irradiation;
  • 13
  • [ 123973-25-1 ]
  • [ 52791-05-6 ]
  • [ 2305154-33-8 ]
YieldReaction ConditionsOperation in experiment
58% In isopropyl alcohol at 80℃; Microwave irradiation;
  • 14
  • [ 28165-50-6 ]
  • [ 52791-05-6 ]
  • 2-bromo-6-[(7,8-dihydro[1,4]dioxino[2,3-g]quinazolin-4-yl)amino]phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In isopropyl alcohol at 80℃; Microwave irradiation;
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