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[ CAS No. 13790-39-1 ] {[proInfo.proName]}

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Chemical Structure| 13790-39-1
Chemical Structure| 13790-39-1
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Product Details of [ 13790-39-1 ]

CAS No. :13790-39-1 MDL No. :MFCD01570172
Formula : C10H9ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LLLHRNQLGUOJHP-UHFFFAOYSA-N
M.W : 224.64 Pubchem ID :2769364
Synonyms :

Calculated chemistry of [ 13790-39-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.53
TPSA : 44.24 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 0.99
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.166 mg/ml ; 0.000739 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.218 mg/ml ; 0.000972 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.21
Solubility : 0.0139 mg/ml ; 0.0000621 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 13790-39-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13790-39-1 ]

* 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 [ 13790-39-1 ]
  • Downstream synthetic route of [ 13790-39-1 ]

[ 13790-39-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 13790-39-1 ]
  • [ 21584-72-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 46, p. 8113 - 8126
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  • [ 13790-39-1 ]
  • [ 13794-72-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide In tetrahydrofuran; water at 75℃; for 24 h; To a solution of 4-chloro-6,7-dimethoxyquinazoline (8.00 g, 35.6 mmol) in 72 mL of H2O and 40 mL of THF was added a solution of KOH (7.0 g, 0.12 mol) in 14 mL of H2O. The mixture was stirred 24 h at 75 °C. Acetic acid (6.4 mL) was added and the precipitate was filtrated and rinsed with H2O and Et2O. A yellow solid (6.64 g) was obtained in 91percent yield. Mp: 300-302 °C; IR (ATR, ZnSe): ν (cm-1) 2822, 1649, 1488, 1272, 1218, 1079, 900, 874, 786, 727; 1H NMR (500 MHz, DMSO-d6): δ (ppm) 12.08 (s, 1H), 7.98 (s, 1H), 7.43 (s, 1H), 7.12 (s, 1H), 3.90 (s, 3H), 3.86 (s, 3H).
13C NMR (126 MHz, DMSO-d6): δ (ppm) 160.1, 154.4, 148.5, 144.9, 143.9, 115.6, 108.0, 104.9, 55.9, 55.7. HRMS-ESI calcd for C10H10N2O3 [M+H]+ 207.0764 found 207.0765.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
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  • [ 591-19-5 ]
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  • [ 153436-54-5 ]
YieldReaction ConditionsOperation in experiment
84% Reflux General procedure: 4-Chloroquinazolines (1 mmol) were dissolved in refluxing2-propanol (20 ml) and the substituted aniline (1 mmol) wasadded drop wise. The reaction mixture was refluxed for 3–4 h, until the reaction was complete as indicated by TLC. The precipitateformed was filtered off and washed with 2-propanol (10 ml) andthen with ether (10 ml). If no precipitate was formed, the solventwas removed under reduced pressure to yield solid product. Theproduct was recrystallized from 75percent ethanol.
Reference: [1] Tetrahedron, 2010, vol. 66, # 4, p. 962 - 968
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7858 - 7873
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1998, vol. 41, # 7, p. 623 - 629
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6373 - 6377
[5] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[6] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 23, p. 2935 - 2940
[7] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 377 - 379
[8] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2106 - 2112
  • 4
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  • [ 179688-53-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 5
  • [ 403-19-0 ]
  • [ 13790-39-1 ]
  • [ 228559-87-3 ]
Reference: [1] Patent: EP1243582, 2002, A1,
  • 6
  • [ 13790-39-1 ]
  • [ 574745-97-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 130 - 149
  • 7
  • [ 638217-08-0 ]
  • [ 13790-39-1 ]
  • [ 1194506-26-7 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetonitrile for 10 h; Reflux EXAMPLE 1
Synthesis of 6-(6,7-dimethoxyquinazolin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide:
To a solution of 4-chloro-6,7-dimethoxyquinazoline (1 equiv.) in 2 ml CH3CN were added 6-hydroxy-N,2-dimethylbenzofuran-3-carboxamide (1 equiv.) and K2CO3 (1.5 equiv.).
The mixture was refluxed under stirring for 10 hr.
After the solvent was evaporated, the residue was washed with water, dried over MgSO4, filtered, concentrated, and purified by column chromatography to give the title compound in a yield of 85percent.
1H NMR (DMSO-d6, 400 MHz) δ: 2.49 (s, 3H), 2.81 (d, J=8.4 Hz, 3H,10), 3.97 (s, 3H), 3.98 (s, 3H), 7.24 (dd, J=2.0, 8.4 Hz, 1H), 7.38 (s, 1H), 7.58 (s, 1H), 7.61 (d, J=2.0 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.96 (m, 1H), 8.52 (s, 1H).
MS(m/e): 394.1 (M+1).
Reference: [1] Patent: US2009/281130, 2009, A1, . Location in patent: Page/Page column 5-6
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  • [ 1188910-76-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1082 - 1105
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