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[ CAS No. 7253-22-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 7253-22-7
Chemical Structure| 7253-22-7
Chemical Structure| 7253-22-7
Structure of 7253-22-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7253-22-7 ]

CAS No. :7253-22-7 MDL No. :MFCD00089492
Formula : C8H4Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :JEBCOVKUVLFOGR-UHFFFAOYSA-N
M.W : 199.04 Pubchem ID :246024
Synonyms :

Calculated chemistry of [ 7253-22-7 ]

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 : 0.0
Molar Refractivity : 49.56
TPSA : 25.78 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) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 3.13
Log Po/w (WLOGP) : 2.94
Log Po/w (MLOGP) : 2.43
Log Po/w (SILICOS-IT) : 3.21
Consensus Log Po/w : 2.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.66
Solubility : 0.0433 mg/ml ; 0.000217 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.0909 mg/ml ; 0.000456 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.57
Solubility : 0.00542 mg/ml ; 0.0000272 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 7253-22-7 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338 UN#:2923
Hazard Statements:H301-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7253-22-7 ]

* 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 [ 7253-22-7 ]
  • Downstream synthetic route of [ 7253-22-7 ]

[ 7253-22-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 16064-14-5 ]
  • [ 7253-22-7 ]
YieldReaction ConditionsOperation in experiment
87% at 110℃; Synthesis of compound 26.3. Into a 50-mL round-bottom flask, were placed compound 26.2 (500 mg, 2.77 mmol, 1.00 equiv), POCl3 (5 mL), N,N-diethylaniline (1.029 g, 6.90 mmol, 2.50 equiv). The resulting solution was stirred for 4 h at 110°C. The reaction mixture was cooled to room temperature and diluted with 50 mL of ice/water. The solids were collected by filtration. And dried in an oven to yield 478 mg (87percent) of compound 26.3.
68% for 2.5 h; Heating / reflux 6-Chloroquinazolin-4-ol (400 mg, 2.21 mmol, 1 eq.), phosphorus oxychloride (1.99 mL, 21.4 mmol, 9.64 eq.) and triethylamine (0.99 mL, 7.11 mmol, 3.21 eq.) were mixed at room temperature under nitrogen and then refluxed for 2.5 hours. Worked up by stripping the reaction, then re-rotovapping the residue 2 times from toluene to obtain brown solids. Methylene chloride (25 mL) was added to dissolve the solids. The organic mixture was then rinsed 2 times with saturated ammonium chloride (25 mL). The organic layer was dried (sodium sulfate) and stripped to give brown solids. The solids were purified over silica gel in 9:1 to 3:1 hexanes/ethyl acetate. Obtained 4,6-dichloroquinazoline (300 mg) as an off-white solid. Yield=68percent. 1H NMR (400 MHz) (DMSO-D6) δ 9.16 (s, 1H): 8.33 (s, 1H), 8.17 (apparent t, 2H, J=7 Hz).
68% With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 100℃; for 3 h; Intermediate 9-b (3 g, 16.61 mmol) was dissolved in CHC13 (30 ml). Oxalyl chloride (2.8 g, 33.22 mmol) and DMF (0.1 ml) were added. The mixture was heated to 100°C for 3 hours. Solvent was evaporated to get intermediate 9 (2.5 g, yield: 68 percent). m/z = 200 (M+H).
Reference: [1] Patent: WO2015/164374, 2015, A1, . Location in patent: Paragraph 00349; 00351
[2] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1401 - 1406
[3] Patent: US2005/54626, 2005, A1, . Location in patent: Page/Page column 38
[4] Patent: WO2016/91774, 2016, A1, . Location in patent: Page/Page column 21
[5] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 7, p. 907 - 911
  • 2
  • [ 16064-14-5 ]
  • [ 7253-22-7 ]
Reference: [1] Synthetic Communications, 2011, vol. 41, # 24, p. 3644 - 3653
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1303
[3] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790
[4] Journal of the Chemical Society, 1947, p. 890,894
[5] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[6] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[7] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[8] Organic Letters, 2010, vol. 12, # 3, p. 552 - 555
[9] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4885 - 4888
[10] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
[11] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1859 - 1866
  • 3
  • [ 16064-14-5 ]
  • [ 7253-22-7 ]
YieldReaction ConditionsOperation in experiment
46% at 100℃; for 1 h; Formamide (4 ml) was added to methyl 2-amino-5-chloro-benzoate (400 mg), and the mixture was stirred with a microwave reactor at 220°C for 20 min. The above reaction was carried out by additional two batches using the same amounts of starting materials. Thereafter, the reaction mixtures were cooled to room temperature and were combined together, and the precipitated crystal was collected by filtration and was washed with ether. The crystal (1.19 g) thus obtained as such was used in the next reaction without further purification. A part (300 mg) of the crystal obtained above was suspended in diisopropylethylamine (1.45 ml), phosphorus oxychloride (0.77 ml) was added to the suspension, and the mixture was stirred at 100°C for one hr. The solvent was removed by distillation under the reduced pressure. Water was added to the reaction mixture under ice cooling, the aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give 4,6-dichloro-quinazoline (151 mg, yield 46percent).
Reference: [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 49
  • 4
  • [ 635-21-2 ]
  • [ 7253-22-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[2] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[3] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 7, p. 907 - 911
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 1303
[5] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790
[6] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1401 - 1406
[7] Patent: WO2016/91774, 2016, A1,
  • 5
  • [ 118-92-3 ]
  • [ 7253-22-7 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1303
[2] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1401 - 1406
  • 6
  • [ 5202-85-7 ]
  • [ 7253-22-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
  • 7
  • [ 5202-89-1 ]
  • [ 7253-22-7 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 890,894
[2] Patent: WO2015/164374, 2015, A1,
[3] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 8
  • [ 77287-34-4 ]
  • [ 635-21-2 ]
  • [ 7253-22-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 4, p. 417 - 420
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