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[ CAS No. 190273-89-3 ] {[proInfo.proName]}

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Chemical Structure| 190273-89-3
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Product Details of [ 190273-89-3 ]

CAS No. :190273-89-3 MDL No. :MFCD04114089
Formula : C8H6BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :IJXKEDDKGGBSBX-UHFFFAOYSA-N
M.W : 224.06 Pubchem ID :2762768
Synonyms :

Safety of [ 190273-89-3 ]

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 [ 190273-89-3 ]

* 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.

  • Upstream synthesis route of [ 190273-89-3 ]
  • Downstream synthetic route of [ 190273-89-3 ]

[ 190273-89-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 593-85-1 ]
  • [ 93777-26-5 ]
  • [ 190273-89-3 ]
YieldReaction ConditionsOperation in experiment
68% at 140℃; Step 1 : 5-Bromo-2-fluorobenzaldehyde (4.0 g, 19.7 mmol, 1.0 equiv) and guanidine carbonate (2.68 g, 29.7 mmol, 1.51 equiv) were dissolved in DMA (20 mL) and heated to 140°C & stirred for overnight. After completion of starting material, reaction mixture was poured onto ice cold water. The solid was filtered, washed with diethyl ether and dried to get 6-bromoquinazolin-2- amine (3.0 g, 68percent) as off white solid. LCMS (ES) m/z = 234.0, 236.0 [M+H]+. H NMR (400 MHz, DMSO-d6) δ 6.96 (s, 2H), 7.34 (d, J = 8.8 Hz, 1 H), 7.74 - 7.77 (m, 1 H), 8.03 (d, J = 2.0 Hz, 1 H), 9.07 (s, 1 H).
60% at 140℃; for 5 h; 2-Fluoro-5-bromobenzaldehyde (10 g, 49.2 mmol) and bisguanidinium carbonate (13.3 g, 74 mmol) were dissolved in N,N-dimethylacetamide (50 mL). The resulting mixture was heated to reflux and stirred for 5 h. After cooling to room temperature, 120 mL water was added and the reaction mixture was allowed to stir for another 2 h at room temperature. The product was collected by filtration and dried under vacuum to afford 6-bromo-2-quinazolinamine (2) (5.0 g, 60percent).
4 g at 160℃; for 0.5 h; To a solution of 5-bromo-2-fluoro-benzaldehyde (20.0 g, 98.5 mmol) in DMA (700 mL) was added guanidine-carbonic acid (26.6 g, 147.7 mmol). The mixture was stirred at 160°C for 0.5 h, cooled to rt and concentrated. The residue was diluted with H20 (300 mL) and extracted with ethyl acetate (200 mL χ 3). The combined organic layers were washed with brine (100 mL x 3), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was washed with DCM (300 mL) to get compound 1A-2 (4.0 g).
Reference: [1] Patent: WO2017/46739, 2017, A1, . Location in patent: Page/Page column 49
[2] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 506 - 518
[3] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3959 - 3962
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 19, p. 5671 - 5686
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 11, p. 3065 - 3068
[6] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 2, p. 385 - 387
[7] Patent: WO2008/20203, 2008, A1, . Location in patent: Page/Page column 72
[8] Patent: WO2018/102751, 2018, A1, . Location in patent: Paragraph 00208
  • 2
  • [ 420-04-2 ]
  • [ 29124-57-0 ]
  • [ 190273-89-3 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With hydrogenchloride In diethyl ether; water for 0.0833333 h;
Stage #2: at 80℃; for 12 h;
70 g of compound IV (0.35 mmol) was added to a 500 ml beaker,Followed by adding 250ml of ether,25ml of 37percent hydrochloric acid for 5 minutes,Filtration,The solid was added to a 500 ml round bottom flask,29 g of cyanamide (0.70 mol) was added,60 ml of N, N-dimethylformamide was added and the oil bath was heated to 80 ° C,TLC monitoring,The reaction was complete after 12 hours,Cooling the reaction system,300 ml of water was added,Filtration,Solid ethyl acetateAnd recrystallized from n-hexane to give the product,Filtered to obtain 56 g of a pale yellow powder of Compound V,Yield 72percent.
Reference: [1] Patent: CN105669566, 2016, A, . Location in patent: Paragraph 0036; 0037; 0038; 0039; 0040; 0041
  • 3
  • [ 93777-26-5 ]
  • [ 190273-89-3 ]
YieldReaction ConditionsOperation in experiment
60% With guanidine carbonate In N,N-dimethyl acetamide at 140℃; for 5 h; Compound 2-Fluoro-5-bromobenzaldehyde (10.0 g, 49.2 mmol)bisguanidiniu carbonate (13.3 g, 74 mmol) were dissolved in N,Ndimethylacetamide(50 mL). The resulting mixture was heated toreflux and stirred for 5 h. After cooling to room temperature,120 mL of water was added and the reaction mixture was allowedto stir for another 2 h at room temperature. The product wascollected by filtration and dried under vacuum to yield 6-Bromo-2-quinazolinamine (12) (5 g, 60percent).
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 275 - 285
  • 4
  • [ 593-85-1 ]
  • [ 93777-26-5 ]
  • [ 190273-89-3 ]
YieldReaction ConditionsOperation in experiment
73% at 150℃; for 5 h; Guanidine carbonate (2) (4.47 g, 36.9 mmol) was added to a solution of 5-bromo-2-fluorobenzaldehyde (1) (5.00 g, 24.6 mmol) in dimethylacetamide (50 ml). The reaction mixture was heated at 150°C for 5 h. The progress of the reaction was monitored by TLC using AcOEt–hexane, 1:1, as eluent. The reaction mixture was cooled and quenched with ice water, and stirred for 30 min. Then the obtained solid was filtered off, and water was removed by azeotropic distillation with PhMe to get 4.00 g (73percent) of compound 3. Mp 270–272°C. 1H NMR spectrum (300 MHz), δ, ppm (J, Hz): 7.04 (2H, s,NH2); 7.37 (1H, d, J = 9.0, H Ar); 7.78 (1H, dd, J = 9.0,J = 2.4, H Ar); 8.05 (1H, d, J = 2.4, H Ar); 9.09 (1H, s,H Ar). Mass spectrum, m/z: 225 [M+H]+.
Reference: [1] Chemistry of Heterocyclic Compounds, 2015, vol. 51, # 1, p. 60 - 66[2] Khim. Geterotsikl. Soedin., 2015, vol. 51, # 1, p. 60 - 66,7
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1996 - 2015
  • 5
  • [ 124-46-9 ]
  • [ 93777-26-5 ]
  • [ 190273-89-3 ]
Reference: [1] Patent: US2006/35897, 2006, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2008/68507, 2008, A2, . Location in patent: Page/Page column 47
[3] Patent: WO2006/52555, 2006, A2, . Location in patent: Page/Page column 32; 73
  • 6
  • [ 3132-99-8 ]
  • [ 190273-89-3 ]
Reference: [1] Patent: CN105669566, 2016, A,
  • 7
  • [ 20357-20-4 ]
  • [ 190273-89-3 ]
Reference: [1] Patent: CN105669566, 2016, A,
  • 8
  • [ 190273-89-3 ]
  • [ 882672-05-1 ]
Reference: [1] Patent: WO2017/46739, 2017, A1, . Location in patent: Page/Page column 49; 50
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