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[ CAS No. 50424-28-7 ] {[proInfo.proName]}

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Chemical Structure| 50424-28-7
Chemical Structure| 50424-28-7
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Product Details of [ 50424-28-7 ]

CAS No. :50424-28-7 MDL No. :MFCD06657615
Formula : C9H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 194.62 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 50424-28-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.04
TPSA : 35.01 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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.152 mg/ml ; 0.000784 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.275 mg/ml ; 0.00141 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0164 mg/ml ; 0.0000841 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 50424-28-7 ]

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 [ 50424-28-7 ]

* 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 [ 50424-28-7 ]
  • Downstream synthetic route of [ 50424-28-7 ]

[ 50424-28-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 19181-64-7 ]
  • [ 50424-28-7 ]
YieldReaction ConditionsOperation in experiment
75% With phosphorus pentachloride In 1,2-dichloro-ethane at 150℃; for 1.11111 h; Microwave irradiation Step 2. Synthesis of 4-chloro-6-methoxy-quinazoline[00247] To 0.852 mmoles of 6-methoxy-3H-quinazolin-4-one in 0.4M soln of DCE, add 1.022 mmoles of PCl5. Microwave at 1500C for 4000 sees. Work-up: The reaction mixture was diluted with CH2Cl2 and washed with water and brine. The organic layer was separated dried over MgSO4, filtered and excess solvent was removed on rotavap to yield the title compound in 75percent yield. The compound was used for the next step without further purification. LC-MS: m/z = 195 (M+ + 1)
Reference: [1] Patent: WO2006/71875, 2006, A1, . Location in patent: Page/Page column 91
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1301
[3] Journal of the Chemical Society, 1947, p. 890,894
[4] Patent: WO2009/63054, 2009, A1, . Location in patent: Page/Page column 48; 108
[5] Organic Letters, 2010, vol. 12, # 3, p. 552 - 555
[6] Patent: US2014/336182, 2014, A1, . Location in patent: Paragraph 0503
[7] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3199 - 3203
  • 2
  • [ 848438-50-6 ]
  • [ 74-88-4 ]
  • [ 50424-28-7 ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 5.5 h; Inert atmosphere; Sealed tube In a seal tube under argon, 16 (80.0 mg, 0.443 mmol) and K2CO3 (91.8 mg, 0.664 mmol) were dissolved in 2.30 mL of DMF. Iodomethane (33.1 μL, 0.532 mmol) was added and the reaction was stirred 5.5 h at 65 °C. H2O was added and the aqueous layer was extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was removed under vacuum. The product was purified by flash column chromatography using hexane/EtOAc (60:40) to afford 17 as a white solid (43.6 mg, 51percent). Mp: 129-131 °C; IR (ATR, ZnSe): ν (cm-1) 2919, 1561, 1494, 1397, 1218, 836, 731, 679; 1H NMR (500 MHz, CDCl3): δ (ppm) 8.90 (s, 1H), 7.93 (d, J = 9.2 Hz, 1H), 7.56 (dd, J = 9.2, 2.8 Hz, 1H), 7.38 (d, J = 2.8 Hz, 1H), 3.97 (s, 3H). C NMR (126 MHz, CDCl3): δ (ppm) 160.5, 159.6, 151.7, 147.4, 130.4, 128.1, 125.2, 102.7, 56.0; HRMS-ESI calcd for C9H8ClN2O [M+H]+ 195.0320 found 195.0313.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 3
  • [ 19181-64-7 ]
  • [ 50424-28-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3081 - 3086
[2] Patent: US2014/235633, 2014, A1, . Location in patent: Paragraph 0095
  • 4
  • [ 6705-03-9 ]
  • [ 50424-28-7 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 890,894
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1301
[3] Patent: US2014/336182, 2014, A1,
  • 5
  • [ 1882-69-5 ]
  • [ 50424-28-7 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 890,894
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1301
  • 6
  • [ 394-31-0 ]
  • [ 50424-28-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3081 - 3086
[2] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 7
  • [ 2475-80-1 ]
  • [ 50424-28-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3081 - 3086
  • 8
  • [ 1882-72-0 ]
  • [ 50424-28-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3081 - 3086
  • 9
  • [ 179688-15-4 ]
  • [ 50424-28-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 10
  • [ 16064-10-1 ]
  • [ 50424-28-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 11
  • [ 179246-11-8 ]
  • [ 50424-28-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 12
  • [ 77287-34-4 ]
  • [ 6705-03-9 ]
  • [ 50424-28-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 4, p. 417 - 420
  • 13
  • [ 50424-28-7 ]
  • [ 2516-95-2 ]
  • [ 6705-03-9 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: US5457105, 1995, A,
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