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Chemical Structure| 19181-53-4
Chemical Structure| 19181-53-4
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Product Details of [ 19181-53-4 ]

CAS No. :19181-53-4 MDL No. :MFCD00673185
Formula : C9H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :JUCDXPIFJIVICL-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :135452442
Synonyms :

Calculated chemistry of [ 19181-53-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.53
TPSA : 46.01 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.3
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 1.92
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.27
Solubility : 0.863 mg/ml ; 0.00539 mol/l
Class : Soluble
Log S (Ali) : -1.87
Solubility : 2.18 mg/ml ; 0.0136 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.13
Solubility : 0.119 mg/ml ; 0.000743 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 19181-53-4 ]

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 [ 19181-53-4 ]

* 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 [ 19181-53-4 ]
  • Downstream synthetic route of [ 19181-53-4 ]

[ 19181-53-4 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 40545-33-3 ]
  • [ 149-73-5 ]
  • [ 19181-53-4 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride In water at 0 - 20℃; for 2 h; Concentrated hydrochloric acid (4.16 mL, 49.9 mmol) was added to a mixture of commercially available 2-amino-5-methylbenzamide 14 (5.00 g, 33.3 mmol) and trimethyl orthoformate (51.0 mL, 466 mmol) at 0 °C and the mixture was stirred at room temperature for 2 h. After the mixture was concentrated under reduced pressure, the residue was diluted with water and neutralized with 2 M aqueous sodium hydroxide solution. The precipitated solid was collected and washed with H2O, methanol and diethyl ether to give 15 as a white powder (4.33 g, 81percent). 1H NMR (300 MHz, DMSO-d6) d 2.44 (3H, s), 7.57 (1H, d, J = 8.4 Hz), 7.62–7.66 (1H, m), 7.91–7.93 (1H, m), 8.03 (1H, s), 12.2 (1H, bs).
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5487 - 5505
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
  • 2
  • [ 52548-14-8 ]
  • [ 6313-33-3 ]
  • [ 19181-53-4 ]
YieldReaction ConditionsOperation in experiment
92% With copper 8-hydroxyquinolinate; sodium hydroxide In water at 100℃; for 0.5 h; Microwave irradiation 1 mmol of 2-iodo-5-methylbenzoic acid, 1 mmol of formamidine hydrochloride, and 8-quinolinolato copper (B ) 0.05 mmol, 1 mmol of sodium hydroxide and 3 mL of water. Placed in the microwave reactor, the microwave reactor at 150 W power heating 100 ° C to 30 minutes, cooled to room temperature. The product was extracted with ethyl acetate and concentrated under reduced pressure. The product was purified by column chromatography to give a white solid in 92percent yield.
Reference: [1] Patent: CN103864702, 2016, B, . Location in patent: Paragraph 0039
  • 3
  • [ 2941-78-8 ]
  • [ 77287-34-4 ]
  • [ 19181-53-4 ]
YieldReaction ConditionsOperation in experiment
78% at 140℃; 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.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 4, p. 847 - 852
[3] Tetrahedron Letters, 2002, vol. 43, # 21, p. 3911 - 3913
[4] Tetrahedron, 2003, vol. 59, # 9, p. 1413 - 1419
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2794 - 2809
[6] Chemische Berichte, 1905, vol. 38, p. 3555
[7] Chemische Berichte, 1901, vol. 34, p. 3366
[8] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[9] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[10] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 662 - 669
[11] Chemistry and Biodiversity, 2018, vol. 15, # 6,
  • 4
  • [ 67-56-1 ]
  • [ 40545-33-3 ]
  • [ 19181-53-4 ]
YieldReaction ConditionsOperation in experiment
90% at 130℃; for 2 h; Inert atmosphere; Microwave irradiation 2-amino-5-methylbenzamide (75 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent),Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube.Microwave tube nitrogen protection,Placed in a single mode pressure microwave synthesizer (Discover CEM,USA). After the reaction mixture was reacted at 130 ° C for 2 hours,Cool to room temperature. Rotary evaporation to remove the solvent,Then, column chromatography (developing solvent: petroleum ether / ethyl acetate)The pure target compound was obtained in a yield of 90percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0035; 0036; 0037; 0038
  • 5
  • [ 2941-78-8 ]
  • [ 19181-53-4 ]
Reference: [1] Patent: US6281227, 2001, B1,
  • 6
  • [ 2941-78-8 ]
  • [ 19181-53-4 ]
Reference: [1] Patent: US5236927, 1993, A,
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 5, p. 1706 - 1712
  • 7
  • [ 1297605-89-0 ]
  • [ 19181-53-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 5, p. 1706 - 1712
  • 8
  • [ 2941-78-8 ]
  • [ 64392-62-7 ]
  • [ 19181-53-4 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 616 - 620
  • 9
  • [ 620-22-4 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1905, vol. 38, p. 3555
[4] Chemische Berichte, 1905, vol. 38, p. 3555
  • 10
  • [ 99-04-7 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1905, vol. 38, p. 3555
  • 11
  • [ 58421-79-7 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3561
  • 12
  • [ 5925-93-9 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3366
  • 13
  • [ 64407-07-4 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1901, vol. 34, p. 3366
  • 14
  • [ 3113-72-2 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
  • 15
  • [ 64113-86-6 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
  • 16
  • [ 7556-94-7 ]
  • [ 19181-53-4 ]
Reference: [1] Proceedings of the National Academy of Sciences of the United States of America, 2017, vol. 114, # 16, p. E3178 - E3187
  • 17
  • [ 19181-53-4 ]
  • [ 58421-79-7 ]
YieldReaction ConditionsOperation in experiment
58% With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 100℃; for 3 h; Intermediate 10-b (2.1 g, 13.11 mmol) was dissolved in CHC13 (30 ml). Oxalyl chloride(1.97 g, 23.26 mmol) and DMF (0.1 ml) were added. The mixture was heated to 100°C for3 hours. The solvent was evaporated to get intermediate 10 (1.5 g, 58 percent).m/z = 179 (M+H).
58% With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 100℃; for 3 h; Intermediate 12-b (2.1 g, 13.11 mmol) was dissolved in CHC13 (30 ml). Oxalyl chloride(1.97 g, 23.26 mmol) and DMF (0.1 ml) were added. The mixture was heated to 100°Cfor 3 hours. The solvent was evaporated to get intermediate 12 (1.5 g, 58 percent).m/z = 179 (M+H).
Reference: [1] Patent: WO2016/91791, 2016, A1, . Location in patent: Page/Page column 20; 21
[2] Patent: WO2016/91774, 2016, A1, . Location in patent: Page/Page column 23; 24
[3] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 44 - 52
  • 18
  • [ 19181-53-4 ]
  • [ 58421-79-7 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 9, p. 1413 - 1419
[2] Synthetic Communications, 2011, vol. 41, # 24, p. 3644 - 3653
[3] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[5] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[6] Patent: WO2006/69395, 2006, A2, . Location in patent: Page/Page column 29
[7] Organic Letters, 2010, vol. 12, # 3, p. 552 - 555
[8] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 662 - 669
[9] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4885 - 4888
  • 19
  • [ 19181-53-4 ]
  • [ 58421-79-7 ]
Reference: [1] Patent: US6281227, 2001, B1,
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