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[ CAS No. 740081-22-5 ] {[proInfo.proName]}

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Chemical Structure| 740081-22-5
Chemical Structure| 740081-22-5
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Product Details of [ 740081-22-5 ]

CAS No. :740081-22-5 MDL No. :MFCD26395271
Formula : C17H13ClFN3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :YJNQYSVKLRFVQN-UHFFFAOYSA-N
M.W : 361.75 Pubchem ID :57476867
Synonyms :

Calculated chemistry of [ 740081-22-5 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.12
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 92.04
TPSA : 73.34 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.33
Log Po/w (XLOGP3) : 3.87
Log Po/w (WLOGP) : 4.52
Log Po/w (MLOGP) : 3.25
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 3.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.66
Solubility : 0.00783 mg/ml ; 0.0000216 mol/l
Class : Moderately soluble
Log S (Ali) : -5.11
Solubility : 0.00283 mg/ml ; 0.00000781 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.95
Solubility : 0.0000407 mg/ml ; 0.000000112 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.77

Safety of [ 740081-22-5 ]

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

Application In Synthesis of [ 740081-22-5 ]

* 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 [ 740081-22-5 ]
  • Downstream synthetic route of [ 740081-22-5 ]

[ 740081-22-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 740081-22-5 ]
  • [ 612501-52-7 ]
YieldReaction ConditionsOperation in experiment
100% With ammonia methyl alcohol In methanol at 20℃; for 2 h; Taking compound 3 (200 mg) dissolved in methanol (2 ml) in, adding methanol and ammonia solution (7 N, 1 ml), then stirred at room temperature 2 hours; the reaction the fluid turns on lathe job to the compound 1 (white powder, 176 mg, quant.).
83% With ammonia; N,N-diethylaniline In methanol at 20℃; for 18 h; To a stirred solution of compound 6 (2.30 g, 5.79 mmol) in MeOH (50 mL) was added concentrated ammonia (4.0 mL). The reaction mixture was stirred at rt for 18 h. The resultant precipitate was filtered, and washed with MeOH to afford 7 (1.54 g, 83percent) as a pale yellow solid, mp 280–282 °C. 1H NMR (DMSO-d6): d 9.75 (s, 1H), 9.48 (s, 1H), 8.35 (s, 1H), 7.66 (s, 1H), 7.52 (t, J = 6.5 Hz, 1H), 7.45 (t,J = 7.0 Hz, 1H), 7.26 (t, J = 8.0 Hz, 1H), 7.21 (s, 1H), 3.98 (s, 3H).
77% With ammonia In methanol; water at 50℃; for 2 h; 6-ACETOXY-4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXYQUINAZOLINE HYDROCHLORIDE FROM step 1 (8.72 g, 21.9 mmol) was dissolved in methanol (200 ml). Concentrated aqueous ammonia (15 ml) was added, and the solution heated to 50°C with stirring for 2 hours, causing precipitation of a cream coloured solid. The solid was collected by filtration, washed with diethyl ether (3x 200 ml), and dried in vacuo at 60°C over diphosphorous pentoxide, giving the product as an off white solid (5.40 g, 77percent); H NMR : 3.95 (s, 3H), 7.19 (s, 1H), 7.23 (dd, 1H), 7.42 (dd, 1H), 7.50 (dd, 1H), 7.64 (s, 1H), 8.32 (s, 1H), 9.43 (s, 1H), 9.67 (br. s, 1H) ; Mass Spectrum: 320.4, 322.4.
77% With ammonia In water at 50℃; for 2 h; 6-ACETOXY-4- (3-CHLORO-2-FLUOROANILINO)-7-METHOXYQUINAZOLINE hydrochloride from step 1 (8.72 g, 21.9 mmol) was dissolved in methanol (200 ml). Concentrated aqueous ammonia (15 ml) was added, and the solution heated to 50°C with stirring for 2 hours, causing precipitation of a cream coloured solid. The solid was collected by filtration, washed with diethyl ether (3x 200 ml), and dried in vacuo at 60°C over diphosphorous pentoxide, giving the product as an off white solid (5.40 g, 77percent). 1H NMR : 3.95 (s, 3H), 7.19 (s, 1H), 7.23 (dd, 1H), 7.42 (dd, 1H), 7.50 (dd, 1H), 7.64 (s, 1H), 8.32 (s, 1H), 9.43 (s, 1H), 9.67 (br. s, 1H); Mass Spectrum : 320.4, 322.4.

Reference: [1] Patent: CN108329276, 2018, A, . Location in patent: Paragraph 0075; 0076
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4455 - 4459
[3] Patent: WO2005/28469, 2005, A1, . Location in patent: Page/Page column 59
[4] Patent: WO2005/28470, 2005, A1, . Location in patent: Page/Page column 54
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4908 - 4912
[6] Patent: WO2014/135876, 2014, A1, . Location in patent: Page/Page column 38
[7] Patent: US2014/255428, 2014, A1, . Location in patent: Paragraph 0224-0225
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