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[ CAS No. 267243-64-1 ] {[proInfo.proName]}

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Chemical Structure| 267243-64-1
Chemical Structure| 267243-64-1
Structure of 267243-64-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 267243-64-1 ]

CAS No. :267243-64-1 MDL No. :MFCD12032146
Formula : C21H21ClFN5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :QVZKEQDJKMFEDU-UHFFFAOYSA-N
M.W : 461.87 Pubchem ID :10600107
Synonyms :

Calculated chemistry of [ 267243-64-1 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.33
Num. rotatable bonds : 8
Num. H-bond acceptors : 8.0
Num. H-bond donors : 1.0
Molar Refractivity : 123.99
TPSA : 105.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.38
Log Po/w (XLOGP3) : 3.97
Log Po/w (WLOGP) : 4.21
Log Po/w (MLOGP) : 3.06
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 3.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.05
Solubility : 0.00415 mg/ml ; 0.00000898 mol/l
Class : Moderately soluble
Log S (Ali) : -5.88
Solubility : 0.000605 mg/ml ; 0.00000131 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.18
Solubility : 0.0000308 mg/ml ; 0.0000000667 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.39

Safety of [ 267243-64-1 ]

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 [ 267243-64-1 ]

* 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 [ 267243-64-1 ]
  • Downstream synthetic route of [ 267243-64-1 ]

[ 267243-64-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 267243-64-1 ]
  • [ 267243-68-5 ]
YieldReaction ConditionsOperation in experiment
50% With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol; dichloromethane at 0 - 20℃; for 0.5 h; [0323] N-(3-chloro-4-fluorophenyl)-7-(3-morpholinopropoxy)-6-nitroquinazolin-4-amine (1.0 eq.) obtained in previous step and NiCl2 6H2O (2.0 eq.) were dissolved in DCM/ MeOH (32 ml:8 ml), the mixture was stirred at 0° C. for 5 min, and NaBH4 (4.0 eq.) was added in batches, then ice bath was removed and the mixture was recovered to room temperature naturally, stirred for further 30 mins. After the reaction finished, the mixture was concentrated to dryness under reduced pressure and gave a crude product which was purified by column chromatography (mobile phase 10:1 DCM/MeOH) to give a light yellow solid of N-(3-chloro-4-fluorophenyl)-7-(3-morpholinopropoxy)-quinazolin-4,6-diamine. (50percent yield). [0324] 1H NMR (500 MHz, DMSO) δ 9.39 (s, 1H), 8.37 (s, 1H), 8.20 (d, J=4.5 Hz, 1H), 7.81 (d, J=8.5 Hz, 1H), 7.41-7.38 (m, 2H), 7.08 (s, 1H), 5.35 (s, 2H), 4.20 (t, J=5.5 Hz, 2H), 3.59 (t, J=4.5 Hz, 4H), 3.18 (d, J=5.0 Hz, 2H), 2.40 (s, 4H), 2.01-1.96 (m, 2H). HRMS (ESI): m/z calcd for (C21H23ClFN5O2+H)+: 432.1603. found: 432.1613.
Reference: [1] Patent: US6344455, 2002, B1,
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 7, p. 1380 - 1397
[3] Patent: US2014/206687, 2014, A1, . Location in patent: Paragraph 0323-0324
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 22, p. 5916 - 5919
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3359 - 3370
[6] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1740 - 1750
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