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Chemical Structure| 194851-16-6
Chemical Structure| 194851-16-6
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Product Details of [ 194851-16-6 ]

CAS No. :194851-16-6 MDL No. :MFCD07838323
Formula : C8H5BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :FUGKKMYSCAYXJJ-UHFFFAOYSA-N
M.W : 225.04 Pubchem ID :135555612
Synonyms :

Calculated chemistry of [ 194851-16-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.06
TPSA : 45.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.381 mg/ml ; 0.00169 mol/l
Class : Soluble
Log S (Ali) : -2.03
Solubility : 2.11 mg/ml ; 0.0094 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.09
Solubility : 0.0181 mg/ml ; 0.0000804 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 194851-16-6 ]

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 [ 194851-16-6 ]

* 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.

  • Upstream synthesis route of [ 194851-16-6 ]
  • Downstream synthetic route of [ 194851-16-6 ]

[ 194851-16-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 20776-50-5 ]
  • [ 77287-34-4 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
89% at 170℃; for 12 h; 0.0 g (1.56 mol) of   2-amino-4-bromobenzoic acid were suspended in 970 ml of   formamide and subsequently stirred at 170° C. for 12 h. Conventional work-up gave 326.0 g of   7-bromo-3H-quinazolin-4-one; HPLC/MS (M+H)+=226 as solid.
71% at 140 - 145℃; for 4 h; 7-bromoquinazolin-4(3H)-oneA mixture of 2-amino-4-bromobenzoic acid (2.0 g) and formamide (1.5 ml) was stirred while heating at 140-145 C. After 4 hours, the reaction mixture was cooled, and 30 ml of water was added causing a solid to precipitate. After collection by filtration, the crude product was pure enough to be used in the next step without further purification. Yield: 1.47 g (6.53 mmol, 71percent). 1H NMR (250 MHz, DMSO) ? (ppm) 8.14 (d, J= 3.0 Hz, 1 H), 8.05 (d, J= 8.5 Hz, 1 H), 7.90 (d, J= 1.9 Hz, 1 H), 7.70 (dd, J= 1.9 Hz, J= 8.5 Hz, 1 H).
36.3% at 150℃; for 1.45 h; Microwave irradiation; Inert atmosphere 2-amino-4-bromobenzoic acid (Compound 4) was reacted with formamide to give 7-bromoquinazolin-4 (3H) -one (Compound 5)5.0 g (23.14 mmol) of 2-amino-4-bromobenzoic acid (Compound 4) was dissolved in 80 ml (2. Olmmol) formamide, Under the protection of nitrogen at 150 ° C, power 300W microwave conditions, reaction 1.45h, after the end of the reaction, the reaction solution by adding ice water, And the mixture was extracted three to four times with ethyl acetate. The extracted organic phase was washed successively with a saturated sodium hydrogencarbonate solution and saturated brine,Dried over sodium sulphate and dried to give a reddish-brown residue, which was chromatographed to give a red brown solid, 7-bromoquinazolin-4 (3H) -one (compound 5), 1.898 in 36.3percent yield;
10.5 g at 190℃; for 10 h; 7-Bromoquinazolin-4(3H)-one (compound A.1)
2-Amino-4-bromobenzoic acid (15.5 g) was dissolved in 100 mL of formamide and the solution was heated at 190° C. for 10 h.
After the reaction was cooled to room temperature, the solid was collected via filtration, rinsed with water, and dried to give 10.5 g of 7-bromo-4-quinazolinone, LCMS ESI(+) m/z: 225/227 (M+1).

Reference: [1] Patent: US2013/12489, 2013, A1, . Location in patent: Paragraph 0182
[2] Patent: WO2010/146173, 2010, A1, . Location in patent: Page/Page column 16
[3] Patent: CN105503744, 2016, A, . Location in patent: Paragraph 0033; 0036; 0037
[4] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[5] Patent: US2016/31860, 2016, A1, . Location in patent: Paragraph 0110; 0111
[6] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 373 - 385
[7] Patent: CN107814773, 2018, A, . Location in patent: Paragraph 0064-0065
  • 2
  • [ 112253-70-0 ]
  • [ 122-51-0 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
71% With trifluoroacetic acid In ISOPROPYLAMIDE at 160℃; for 0.5 h; Microwave radiation To a solution of 2-amino-4-bromo-benzamide (1 equiv) in DMA (0.14 M) were added triethyl orthoformate (10 equiv) and trifluoroacetic acid (1 equiv). The reaction vessel was sealed and exposed to microwave radiation (160 0C, medium absorption setting) for 30 minutes. The reaction mixture was concentrated in vacuo and the residue was filtered through a silica pad with 10 percent methanol in ethyl acetate yielding the required product as a pale yellow solid. <n="121"/>7-Bromo-3H-quinazolin-4-one: (71 percent yield, 100 percent purity) m/z (LC-MS, ESP): 268 [M+H]+ R/T = 2.94 min
Reference: [1] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 119-120
  • 3
  • [ 67-56-1 ]
  • [ 112253-70-0 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
80% at 130℃; for 2 h; Microwave irradiation; Inert atmosphere 2-Amino-4-bromobenzamide (107 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent),Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Rotary evaporation to remove the solvent,Pure target compound was then obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 80percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0085; 0086; 0087; 0088
  • 4
  • [ 112253-70-0 ]
  • [ 109-94-4 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
84% With sodium methylate In ethanol for 1.5 h; Heating / reflux 2) 4-Bromoanthranilic amide (40 g, 186 mmol) obtained in 1) was dissolved in ethanol (400 mL). Thereto was added sodium methoxide (54.2 g, 93 mmol) with stirring under ice-cooling and then ethyl formate (60.1 mL, 744 mmol) was added dropwise. The mixture was heated under reflux for 1.5 hrs. The reaction mixture was allowed to cool to room temperature and water (500 mL) was added and then acetic acid (40 mL) was added. The mixture was concentrated under reduced pressure and water (200 mL) was added. The precipitate was collected by filtration and dried to give 7-bromo-3H-quinazolin-4-one (35 g, 156 mmol, 84percent). 7-bromo-3H-quinazolin-4-one [0153] 1H NMR (DMSO-d6) δ ppm: 7.68 (dd, J=1.7, 8.5 Hz, 1H), 7.88 (d, J=1.7 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 8.14 (s, 1H).
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 32
  • 5
  • [ 20776-50-5 ]
  • [ 3473-63-0 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
98% for 13 h; Heating / reflux 3) Formamidine acetate (1.96 g, 18.9 mmol) and 2-ethoxyethanol (25 mL) were added to 4-bromoanthranyl acid (1.63 g, 7.55 mmol) and the mixture was heated under reflux for 7 hrs. Formamidine acetate (1.45 g) was added and the mixture was further refluxed for 6 hrs. Dilute aqueous ammonia solution (30 mL) was added, and after stirring for a while, the product was collected by filtration and dried to give the objective 7-bromo-3H-quinazolin-4-one (1.67 g, 98percent). [CHEMMOL-00362] [0144] 1H NMR (DMSO-d6) δ ppm: 7.69 (dd, J=1.9, 8.4 Hz, 1H), 7.89 (d, J=1.9 Hz, 1H), 8.04 (d, J=8.4 Hz, 1H), 8.14 (br s, 1H).
Reference: [1] Patent: US2004/116422, 2004, A1, . Location in patent: Page/Page column 31
  • 6
  • [ 194851-17-7 ]
  • [ 20776-50-5 ]
  • [ 194851-16-6 ]
Reference: [1] Patent: US5814630, 1998, A,
  • 7
  • [ 20776-50-5 ]
  • [ 68-12-2 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
36.3% at 150℃; for 1.45 h; Inert atmosphere; Microwave irradiation (23.14 mmol) of 2-amino-4-bromobenzoic acid was dissolved in 80 ml (2.01 mmol) of formamide and reacted under nitrogen at 150 ° C under a microwave power of 300 W for 1.45 h. After completion of the reaction, The reaction solution was added to ice water and extracted with ethyl acetate for 3-4 times. The extracted organic phase was washed successively with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then spin dried to give a reddish brown residue , And the reddish brown residue was separated on a chromatographic column to give 1.89 g of a reddish brown solid 7-bromoquinazolin-4 (3H) -one in 36.3percent yield.
Reference: [1] Patent: CN105859638, 2016, A, . Location in patent: Paragraph 0036; 0037
  • 8
  • [ 77287-34-4 ]
  • [ 5794-88-7 ]
  • [ 194851-16-6 ]
YieldReaction ConditionsOperation in experiment
41.24% at 150℃; for 1.5 h; Inert atmosphere; Microwave irradiation Around bottom two flask charged with 2-amino-5-bromobenzoicacid 12 (5.00 g, 23.14 mmol) was flushed with nitrogen and suspended in HCONH2 (80 mL, 2.01 mmol), the mixture was stirred at 150 °C for 1.5 h by atmospheric microwave heating. The product was extracted with AcOEt (50 mL x 3), washed with water, and dried over Na2SO4. After filtration and concentration in vacuo, the residue was purified by silica gel flash chromatography (PE/AcOEt = 5:1) affording 13 (1.46 g, 41.24percent) as white solid. mp: 259-261 °C.
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 506 - 518
  • 9
  • [ 99277-71-1 ]
  • [ 77287-34-4 ]
  • [ 194851-16-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 288 - 292
  • 10
  • [ 194851-16-6 ]
  • [ 573675-55-5 ]
YieldReaction ConditionsOperation in experiment
81% at 115℃; for 3 h; 20.4 ml (0.12 mol) of   N-ethyldiisopropylamine were slowly added to a suspension of 55.0 g (0.24 mol) of   7-bromo-3H-quinazolin-4-one in 300 ml of   phosphorus oxytrichloride. The reaction mixture was stirred at 115° C. for 3 h and subsequently allowed to come to room temperature. Conventional work-up gave 48.0 g of   7-bromo-4-chloroquinazoline; HPLC/MS (M+H)+=244 as solid
76% for 4 h; Reflux 7-bromo-4-chloroquinazoline7-bromoquinazolin-4(3H)-one (1.46 g), ?/,?/-diisopropylethylamine (1.24 ml) and POCI3 (5 ml) were heated at reflux. After 4 hours, the warm product was poured over crushed ice and diluted with DCM. The aqueous layer was extracted with DCM and the combined organic layers were washed with brine and dried over Na2SO4. Evaporation of the organics gave the crude product that was filtered over a pad of silica with EtOAc as eluent. Removal of the solvent gave the title compound in high purity. Yield: 1.21 g (4.93 mmol, 76percent). 1H NMR (250 MHz, CDCI3) ? (ppm) 9.03 (s, 1 H), 8.25 (d, J= 1.9 Hz, 1 H), 8.11 (d, J= 8.9 Hz, 1 H), 7.81 (dd, J= 1.9 Hz, J= 8.9 Hz, 1 H).
Reference: [1] Patent: US2013/12489, 2013, A1, . Location in patent: Paragraph 0183
[2] Patent: WO2010/146173, 2010, A1, . Location in patent: Page/Page column 16-17
[3] Patent: WO2005/42498, 2005, A2, . Location in patent: Page/Page column 43
[4] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1859 - 1866
  • 11
  • [ 194851-16-6 ]
  • [ 573675-55-5 ]
YieldReaction ConditionsOperation in experiment
97% Reflux To a solution of 7-bromoquinazolin-4-ol (2.88 g, 12.8 mmol) in POCl3 (30 mL) was added PCl5 (4 g, 19.2 mmol). The mixture was stirred at reflux overnight. After cooling to room temperature, the mixture was concentrated. The residue was dissolved in CH2Cl2 and treated with saturated aqueous NaHCO3 solution. A precipitate that formed was filtered off from the mixture. The organic layer was washed with brine, dried and concentrated to give 7-bromo-4-chloroquinazoline (3 g, 97percent). 1H NMR (DMSO-d6) δ 8.36 (s, IH), 8.01 (d, J- 8.40Hz, IH), 7.88 (d, J = 1.60 Hz, IH), 7.69 (dd, J= 8.80 Hz, 1.60 Hz, IH).
84% for 4 h; Reflux Compound 102 (14.4 g) was dissolved in thionyl chloride (50 ml)Adding 1 mL of the catalytic amount of anhydrous DMF,The reaction was refluxed for 4 hours.After completion of the reaction, excess thionyl chloride was distilled off under reduced pressure to give Compound 103. Yield 92.4percent.
Reference: [1] Patent: WO2009/111028, 2009, A1, . Location in patent: Page/Page column 48
[2] Patent: CN106317026, 2017, A, . Location in patent: Paragraph 0075; 0076; 0077; 0078; 0368-0371
[3] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10554 - 10560
[4] Patent: WO2015/103317, 2015, A1, . Location in patent: Page/Page column 313; 314
  • 12
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  • [ 1123169-43-6 ]
Reference: [1] Patent: WO2015/103317, 2015, A1,
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