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[ CAS No. 17329-31-6 ] {[proInfo.proName]}

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Chemical Structure| 17329-31-6
Chemical Structure| 17329-31-6
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Product Details of [ 17329-31-6 ]

CAS No. :17329-31-6 MDL No. :MFCD01219542
Formula : C8H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :MAIZCACENPZNCN-UHFFFAOYSA-N
M.W :161.16 Pubchem ID :135478037
Synonyms :

Calculated chemistry of [ 17329-31-6 ]

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 : 2.0
Molar Refractivity : 46.77
TPSA : 71.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.72
Log Po/w (XLOGP3) : 0.09
Log Po/w (WLOGP) : 0.51
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 0.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.51
Solubility : 4.95 mg/ml ; 0.0307 mol/l
Class : Very soluble
Log S (Ali) : -1.15
Solubility : 11.4 mg/ml ; 0.0705 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.22 mg/ml ; 0.00136 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 17329-31-6 ]

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 [ 17329-31-6 ]

* 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 [ 17329-31-6 ]
  • Downstream synthetic route of [ 17329-31-6 ]

[ 17329-31-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 6943-17-5 ]
  • [ 17329-31-6 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In methanol at 20℃; for 4 h; Intermediate 5 [00201] In a 1 L flask was added Intermediate 5A (1 g, 5.23 mmol) in MeOH(500ml) to give a yellow suspension. 10percent Pd/C (0.056 g, 0.523 mmol) was added. The mixture was stirred at r.t. under a hydrogen balloon for 4 hours. The reaction mixture was filtered and concentrated to a yellow solid 0.84 g (100percent). 1H NMR (500 MHz, DMSO-d6) δ ppm 5.60 (s, 2 H) 7.05 (dd, J=8.80, 2.75 Hz, 1 H) 7.16 (d, J=2.75 Hz, 1 H) 7.36 (d, J=8.80 Hz, 1 H) 7.74 (s, 1 H) 11.80 (s, 1 H).
100% With hydrogen In methanol at 20℃; for 4 h; Intermediate 4; [00201] In a 1 L flask was added Intermediate 4A (1 g, 5.23 mmol) in MeOH(500 mL) to give a yellow suspension. 10percent Pd/C (0.056 g, 0.523 mmol) was added. The mixture was stirred at rt under a hydrogen balloon for 4 h. The reaction mixture was filtered and concentrated to a yellow solid 0.84 g (100percent). 1H NMR (500 MHz, DMSO-d6) δ ppm 5.60 (s, 2 H) 7.05 (dd, J=8.80, 2.75 Hz, 1 H) 7.16 (d, J=2.75 Hz, 1 H) 7.36 (d, J=8.80 Hz, 1 H) 7.74 (s, 1 H) 11.80 (s, 1 H).
73% With stannous chloride dihydrate In ethyl acetate for 8 h; Reflux General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
30% With tin(II) chloride dihdyrate In methanol for 3 h; Reflux; Inert atmosphere A mixture of 1 g (5 mmol) of 6-nitroquinazolin-4-(3H)-one 11 and 6 g (25 mmol) of SnCl2·2H2O in 25 mL methanol was heated to reflux for 3 h while stirring under argon. The solvent was evaporated then 200 mL saturated aqueous NaHCO3 solution were added to the residue and left stirring for 10 min. The suspension was then filtered and the aqueous filtrate was collected and evaporated. The product was then extracted from the residue using DMF and purified using column chromatography (90percent DCM, 10percent 0.5 M NH3 in methanol solution) to give the pure compound 12. Yield: 30percent; mp: 310–312 °C; 1H-NMR (200 MHz, DMSO-d6) δ: 11.80 (s, 1H), 7.74 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.17 (d, J=2.2 Hz, 1H), 7.05 (dd, J=8.7,2.4 Hz, 1H), 5.59 (s, 2H); 13C-NMR (50 MHz, DMSO-d6) δ: 161.03, 148.20, 140.63, 139.97, 128.38, 123.99, 122.49, 106.48; MS (ESI): m/z=161.9 (M+H)+.

Reference: [1] Patent: WO2008/79759, 2008, A1, . Location in patent: Page/Page column 90
[2] Patent: WO2008/79836, 2008, A2, . Location in patent: Page/Page column 86
[3] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[4] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[5] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 12, p. 1166 - 1172
[6] Yakugaku Zasshi, 1942, vol. 62, p. 66,68; dtsch. Ref. S. 24[7] Chem.Abstr., 1951, p. 1580
[8] Yakugaku Zasshi, 1942, vol. 62, p. 66,68; dtsch. Ref. S. 24[9] Chem.Abstr., 1951, p. 1580
[10] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[11] Patent: WO2006/12374, 2006, A1, . Location in patent: Page/Page column 181
[12] Patent: US6339099, 2002, B1, . Location in patent: Page column 43, 44
[13] Patent: US2003/225106, 2003, A1, . Location in patent: Page 86
[14] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 11, p. 3235 - 3239
  • 2
  • [ 616-79-5 ]
  • [ 17329-31-6 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
  • 3
  • [ 17420-30-3 ]
  • [ 17329-31-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 12, p. 1166 - 1172
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