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Chemical Structure| 31374-18-2
Chemical Structure| 31374-18-2
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Product Details of [ 31374-18-2 ]

CAS No. :31374-18-2 MDL No. :MFCD00115130
Formula : C8H5ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :PMLONMIODRHERC-UHFFFAOYSA-N
M.W : 180.59 Pubchem ID :135416175
Synonyms :

Calculated chemistry of [ 31374-18-2 ]

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 : 1.0
Molar Refractivity : 47.37
TPSA : 45.75 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) : -6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.19
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.58
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 2.72
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.629 mg/ml ; 0.00348 mol/l
Class : Soluble
Log S (Ali) : -1.96
Solubility : 1.96 mg/ml ; 0.0108 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.85
Solubility : 0.0255 mg/ml ; 0.000141 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 31374-18-2 ]

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 [ 31374-18-2 ]

* 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 [ 31374-18-2 ]
  • Downstream synthetic route of [ 31374-18-2 ]

[ 31374-18-2 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 3473-63-0 ]
  • [ 89-77-0 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
95% Microwave irradiation 10g of compound BB1, formamidine acetate 8g (1.3eq) into 100ml eggplant-shaped flask, uniformly mixed, the microwave reaction 4πη (60percent power). After cooling, 30ml of water was added, the solid was washed and filtered to give the BB2 compound 10g, yield 95percent.
88.1% at 120℃; for 16 h; 4-Chloro-2-aminobenzoic acid(10.26, 60.0mmol) and formamidine acetate (12.5g, 120.0mmol]Into the 250mL ethylene glycol monomethyl ether, heated to 120 ° C, insulation reaction 16h,Cooled to room temperature, concentrated to dryness under reduced pressure,Washed with 0.0lmol / L ammonia to neutral, filtered and dried to give an off-white solid of 7-chloro-3H-quinazolin-4-one in a yield of 88.1percent
Reference: [1] Patent: CN103570738, 2016, B, . Location in patent: Paragraph 0303; 0304; 0306
[2] Patent: CN103382182, 2016, B, . Location in patent: Paragraph 0272-0275
[3] Patent: WO2012/88712, 2012, A1, . Location in patent: Page/Page column 16
[4] MedChemComm, 2015, vol. 6, # 1, p. 222 - 229
  • 2
  • [ 5900-59-4 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
77% With hydrogenchloride In water; trimethyl orthoformate Reference example 2: 7-chloro-4(3H)-quinazolone
2-Amino-4-chlorobenzamide (25.6 g, 0.150 mol) obtained in Reference example 1 was dissolved in trimethyl orthoformate (560 ml), and to this added was concentrated hydrochloric acid (15 ml), and the mixture was stirred at room temperature for 1 hour.
After completion of the reaction, the reaction solution was filtered, and the crude crystal filtered was suspended in water (250 ml) and neutralized with 3N NaOH aqueous solution.
The neutralized solution was filtered, the solid being washed with water on the funnel to give 20.9 g (yield 77percent) of the title compound as white crystal.
Reference: [1] Patent: EP1229025, 2002, A1,
  • 3
  • [ 67-56-1 ]
  • [ 5900-59-4 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
70% at 130℃; for 2 h; Inert atmosphere; Microwave irradiation 2-Amino-4-chlorobenzamide (85 mg, 0.5 mmol), [Cp * Ir (2,2'-bpyO)(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.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Rotary evaporation to remove the solvent,Pure target compound was then obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 70percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337646, 2017, A, . Location in patent: Paragraph 0070; 0071; 0072; 0073
  • 4
  • [ 77287-34-4 ]
  • [ 89-77-0 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
96.1% at 150℃; for 2 h; Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.
90.7% at 130 - 160℃; for 5 h; At room temperature,Add p-chloroanthranilic acid (20 g, 116.56 mmol) to a 250 ml round bottom flask.Add formamide (50 mL, 1.26 mol),Heating to 130 ° C, and then heating up to 160 ° C when completely dissolved,The reaction was carried out for 5 h, and the reaction was completed by TLC. After cooling to room temperature, the reaction solution was poured into 400 ml of ice water and stirred.A large amount of solid is produced, suction filtered, dried, and recrystallized from ethanol to give an off-white intermediate 419.1g, yield 90.7percent,
87.7% at 130 - 190℃; for 4.5 h; A mixture of compound 0301(17.2 g, 100 mmol) and formamide (20 mL) was stirred at 130 0C for 30 minutes and to 190 0C for 4 hours. The mixture was allowed to cool to room temperature. It was then poured into a mixture of ice and water. The precipitate was isolated, washed with water and dried to give the title compound 0302 (15.8 g, 87.7percent). 1H NMR (DMSO-J6): δ 7.65 (dd, IH), 7.72 (d, IH), 8.12 (d, IH), 8.36 (s, IH).
87.7% at 130 - 190℃; for 4.5 h; Example 22Preparation of N1-(4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazolin-6-yl)-N5-hydroxyglutaramide (Compound 38)Step 22a. 7-Chloroquinazolin-4 (3H)-one (Compound 0302); A mixture of compound 0301 (17.2 g, 100 mmol) and formamide (20 mL) was stirred at 130° C. for 30 minutes and to 190° C. for 4 hours. The mixture was allowed to cool to room temperature. It was then poured into a mixture of ice and water. The precipitate was isolated, washed with water and dried to give the title compound 0302 (15.8 g, 87.7percent). 1H NMR (DMSO-d6): δ 7.65 (dd, 1H), 7.72 (d, 1H), 8.12 (d, 1H), 8.36 (s, 1H).
83% 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.
19.1 g for 4 h; Reflux General procedure: 6,7-dimethoxyquinazolin-4(3H)-one (6a) was prepared accordingto a similar procedure of Luth and Lowe [62], with formamidein replace of formamidine acetate. Briefly, a solution of 5a(5 g, 25.4 mmol) in formamide (30 mL) was heated to reflux for 4 h,cooled to rt and poured onto ice-water, extracted with ethyl acetate,washed with brine and dried over Na2SO4, After removal of thesolvent, the residue was purified by silica gel column to give 6,7-dimethoxyquinazolin-4(3H)-one (6a) as a white solid (4.5 g, yield86percent). mp 310-312 °C (reference mp 300 °C [64]).

Reference: [1] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[2] Heterocyclic Communications, 2001, vol. 7, # 4, p. 337 - 340
[3] Patent: CN108484574, 2018, A, . Location in patent: Paragraph 0130; 0131; 0132
[4] Cell Chemical Biology, 2017, vol. 24, # 12, p. 1490 - 11,1500
[5] Patent: WO2008/33747, 2008, A2, . Location in patent: Page/Page column 129
[6] Patent: US2009/111772, 2009, A1, . Location in patent: Page/Page column 73
[7] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[8] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4096 - 4109
[9] Journal of the American Chemical Society, 1946, vol. 68, p. 1305
[10] Huaxue Xuebao, 1956, vol. 22, p. 335,336[11] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
[12] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[13] Journal of the Chemical Society, 1947, p. 890,894
[14] Patent: US2005/165032, 2005, A1, . Location in patent: Page/Page column 9
[15] Patent: US2008/300248, 2008, A1, . Location in patent: Page/Page column 7
[16] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3851 - 3855
[17] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[18] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 5
  • [ 77287-34-4 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
87.7% at 130 - 190℃; for 4.5 h; Step 22a.
7-Chloroquinazolin-4(3H)-one (Compound 0302)
A mixture of compound 0301 (17.2 g, 100 mmol) and formamide (20 mL) was stirred at 130° C. for 30 minutes and to 190° C. for 4 hours.
The mixture was allowed to cool to room temperature.
It was then poured into a mixture of ice and water.
The precipitate was isolated, washed with water and dried to give the title compound 0302 (15.8 g, 87.7percent).
1H NMR (DMSO-d6): δ 7.65 (dd, 1H), 7.72 (d, 1H), 8.12 (d, 1H), 8.36 (s, 1H).
Reference: [1] Patent: US2009/76022, 2009, A1, . Location in patent: Page/Page column 74
  • 6
  • [ 153437-17-3 ]
  • [ 111-90-0 ]
  • [ 89-77-0 ]
  • [ 31374-18-2 ]
Reference: [1] Patent: US5952333, 1999, A,
  • 7
  • [ 5900-58-3 ]
  • [ 77287-34-4 ]
  • [ 31374-18-2 ]
YieldReaction ConditionsOperation in experiment
84.1% at 150℃; for 2 h; Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.
Reference: [1] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[2] MedChemComm, 2014, vol. 5, # 9, p. 1290 - 1296
[3] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 8
  • [ 942319-20-2 ]
  • [ 463-52-5 ]
  • [ 31374-18-2 ]
Reference: [1] Synthesis, 2008, # 24, p. 3974 - 3980
  • 9
  • [ 89-77-0 ]
  • [ 31374-18-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 817 - 821
[2] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 817 - 821
[3] Patent: EP1990337, 2008, A1, . Location in patent: Page/Page column 11
  • 10
  • [ 5900-59-4 ]
  • [ 144-62-7 ]
  • [ 31374-18-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342
  • 11
  • [ 5900-59-4 ]
  • [ 122-51-0 ]
  • [ 31374-18-2 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 184
  • 12
  • [ 6313-33-3 ]
  • [ 89-77-0 ]
  • [ 31374-18-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3860 - 3873
  • 13
  • [ 38487-86-4 ]
  • [ 68-12-2 ]
  • [ 31374-18-2 ]
  • [ 13165-35-0 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
  • 14
  • [ 64392-62-7 ]
  • [ 89-77-0 ]
  • [ 31374-18-2 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 616 - 620
  • 15
  • [ 123-91-1 ]
  • [ 5900-59-4 ]
  • [ 122-51-0 ]
  • [ 31374-18-2 ]
Reference: [1] Patent: US2003/64986, 2003, A1,
  • 16
  • [ 2516-95-2 ]
  • [ 16712-16-6 ]
  • [ 31374-18-2 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 34, p. 6517 - 6521
  • 17
  • [ 77287-34-4 ]
  • [ 31374-18-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 817 - 821
  • 18
  • [ 77287-34-4 ]
  • [ 31374-18-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2002, vol. 38, # 7, p. 817 - 821
  • 19
  • [ 6280-88-2 ]
  • [ 31374-18-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 20
  • [ 74-11-3 ]
  • [ 31374-18-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
  • 21
  • [ 5900-59-4 ]
  • [ 149-73-5 ]
  • [ 31374-18-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
  • 22
  • [ 31374-18-2 ]
  • [ 2148-57-4 ]
YieldReaction ConditionsOperation in experiment
94.828% at 100℃; for 3 h; 7-Chloro-3H- quinazolin-4-one (170, 0.155 g, 0.85830 mmol) was dissolved in 1 mL of POCI3 in a screw cap vial. The vial was sealed and placed in a 100 °C oil bath for 3 hours. The resulting solution was concentrated under vacuum and co-concentrated from toluene three times to provide the desired compound (171, 0.162 g, 0.81391 mmol, 94.828percent). MS: 199.0 m/z (M+H)+.
Reference: [1] Patent: WO2013/142613, 2013, A1, . Location in patent: Page/Page column 175
[2] Synthetic Communications, 2011, vol. 41, # 24, p. 3644 - 3653
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 12, p. 1084 - 1087
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[5] Organic Letters, 2010, vol. 12, # 3, p. 552 - 555
[6] Patent: WO2012/88712, 2012, A1, . Location in patent: Page/Page column 16
[7] MedChemComm, 2014, vol. 5, # 9, p. 1290 - 1296
[8] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3851 - 3855
[9] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4885 - 4888
[10] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443
  • 23
  • [ 31374-18-2 ]
  • [ 2148-57-4 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 7, p. 907 - 911
[2] Patent: WO2014/145512, 2014, A2, . Location in patent: Page/Page column 97
  • 24
  • [ 38487-86-4 ]
  • [ 68-12-2 ]
  • [ 31374-18-2 ]
  • [ 13165-35-0 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
  • 25
  • [ 31374-18-2 ]
  • [ 53449-14-2 ]
YieldReaction ConditionsOperation in experiment
72% at 0 - 90℃; for 3 h; To a 100-mL flask was added concentrated sulfuric acid (10 mL),concentrated nitric acid (5 mL) and 6b (10 g, 55.4 mmol) understirring at 0 C. The mixture was heated and stirred at 90 C for 3 h.After cooling to rt, the mixture was poured onto ice-water, filtered,washed with water, dried. The crude product was recrystallizedfrom acetic acid to afford 7-chloro-6-nitroquinazolin-4(3H)-one(6c) as a light yellow solid (9 g, yield 72percent). mp 315e316 C; 1H NMR(DMSO-d6, ppm): d 12.79 (b, 1H), 8.67 (s, 1H), 8.31 (s, 1H), 8.01 (s,1H).
71.2% at 90℃; for 3 h; Cooling with ice 200 mL of concentrated sulfuric acid was placed in a 500 mL single-mouth round bottom flask under ice bath, and stirred.Slowly add 20 mL of concentrated nitric acid to concentrated sulfuric acid.After stirring for 30 min, it was slowly added dropwise to Intermediate 4 (50 g, 0.28 mol, 1 eq) using a constant pressure dropping funnel.The reaction solution was yellowish brown, most of the raw materials were insoluble, and the temperature was slowly raised to 90 ° C, and the reaction was carried out for 3 hours, and the reaction was completely confirmed by TLC. After cooling to room temperature, the reaction solution was poured into 3 L of ice water, stirred for 30 min, suction filtered, and the filter cake was washed with water.Drying, recrystallization from glacial acetic acid gave 44.5 g of a yellow solid.Yield 71.2percent,
68.3% at 20 - 45℃; Under ice-water bath cooling,A solution of 7-chloro-3H-quinazolin-4-one (9.00 g, 50.0 mmol)(Concentrated sulfuric acid 30mL and fuming nitric acid 30mL), plus complete, stirring at room temperature lh,Heat to 45 ° C and stir overnight. The reaction solution was then poured into 60 mL of ice water, filtered and the resulting solid was filtered and washed with water, recrystallized from acetic acid, dried,To give 7.78 g of 7-chloro-6-nitro-3H-quinazolin-4-one as a yellow solid in 68.3percent yield.
62.7% With sulfuric acid; nitric acid In water at 0 - 45℃; Compound 0302 (18.0 g, 100 mmol) was added portionwise to a stirred mixture of concentrated sulfuric acid (60 mL) and fuming nitric acid (60 mL) which had been cooled to 0 0C, the mixture was stirred at ambient temperature for 1 hour and then heated to 45 0C overnight. The mixture was poured into the mixture of ice and water. The precipitate was isolated, washed with water and dried. Recrystallization from acetic acid to give the title compound 0303 (14.1 g, 62.7percent). 1H NMR (DMSO-J6): δ 8.00 (s, IH), 8.27 (s, IH), 8.65 (s, IH), 12.70 (s, IH).
62.7% at 0 - 45℃; Step 22b.
7-Chloro-6-nitroquinazolin-4(3H)-one (compound 0303)
Compound 0302 (18.0 g, 100 mmol) was added portionwise to a stirred mixture of concentrated sulfuric acid (60 mL) and fuming nitric acid (60 mL) which had been cooled to 0° C., the mixture was stirred at ambient temperature for 1 hour and then heated to 45° C. overnight.
The mixture was poured into the mixture of ice and water.
The precipitate was isolated, washed with water and dried.
Recrystallization from acetic acid to give the title compound 0303 (14.1 g, 62.7percent).
1H NMR (DMSO-d6): δ 8.00 (s, 1H), 8.27 (s, 1H), 8.65 (s, 1H), 12.70 (s, 1H).
62.7% at 0 - 45℃; Step 22b. 7-Chloro-6-nitroquinazolin-4(3H)-one (compound 0303); Compound 0302 (18.0 g, 100 mmol) was added portionwise to a stirred mixture of concentrated sulfuric acid (60 mL) and fuming nitric acid (60 mL) which had been cooled to 0° C., the mixture was stirred at ambient temperature for 1 hour and then heated to 45° C. overnight. The mixture was poured into the mixture of ice and water. The precipitate was isolated, washed with water and dried. Recrystallization from acetic acid to give the title compound 0303 (14.1 g, 62.7percent). 1H NMR (DMSO-d6): δ 8.00 (s, 1H), 8.27 (s, 1H), 8.65 (s, 1H), 12.70 (s, 1H).

Reference: [1] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4096 - 4109
[2] European Journal of Medicinal Chemistry, 2018, vol. 147, p. 227 - 237
[3] Patent: CN108484574, 2018, A, . Location in patent: Paragraph 0133; 0134; 0135
[4] Patent: CN103382182, 2016, B, . Location in patent: Paragraph 0272; 0273; 0276; 0277
[5] Patent: WO2008/33747, 2008, A2, . Location in patent: Page/Page column 129
[6] Patent: US2009/76022, 2009, A1, . Location in patent: Page/Page column 74
[7] Patent: US2009/111772, 2009, A1, . Location in patent: Page/Page column 73
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[9] Patent: EP1229025, 2002, A1,
[10] Patent: EP1990337, 2008, A1, . Location in patent: Page/Page column 11
[11] Patent: US2008/300248, 2008, A1, . Location in patent: Page/Page column 7
[12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7988 - 7998
[13] Patent: CN103570738, 2016, B, . Location in patent: Paragraph 0303; 0304; 0307
  • 26
  • [ 31374-18-2 ]
  • [ 55496-69-0 ]
Reference: [1] Patent: CN103382182, 2016, B,
[2] Patent: US2009/111772, 2009, A1,
  • 27
  • [ 31374-18-2 ]
  • [ 179552-73-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7988 - 7998
[2] Patent: CN103570738, 2016, B,
  • 28
  • [ 31374-18-2 ]
  • [ 179552-75-1 ]
Reference: [1] Patent: US2009/111772, 2009, A1,
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Similarity: 0.86

Chemical Structure| 75844-41-6

[ 75844-41-6 ]

5-Methylquinazolin-4(1H)-one

Similarity: 0.82

Chemical Structure| 7142-09-8

[ 7142-09-8 ]

6-Chloro-2-methylquinazolin-4(3H)-one

Similarity: 0.80

Chemical Structure| 18731-19-6

[ 18731-19-6 ]

2,6-Dimethylquinazolin-4(1H)-one

Similarity: 0.78

Chemical Structure| 6958-39-0

[ 6958-39-0 ]

6,7-Dichloroquinazolin-4(3H)-one

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Related Parent Nucleus of
[ 31374-18-2 ]

Quinazolines

Chemical Structure| 150454-06-1

[ 150454-06-1 ]

4-Oxo-1,4-dihydroquinazoline-6-carboxamide

Similarity: 0.86

Chemical Structure| 75844-41-6

[ 75844-41-6 ]

5-Methylquinazolin-4(1H)-one

Similarity: 0.82

Chemical Structure| 7142-09-8

[ 7142-09-8 ]

6-Chloro-2-methylquinazolin-4(3H)-one

Similarity: 0.80

Chemical Structure| 18731-19-6

[ 18731-19-6 ]

2,6-Dimethylquinazolin-4(1H)-one

Similarity: 0.78

Chemical Structure| 6958-39-0

[ 6958-39-0 ]

6,7-Dichloroquinazolin-4(3H)-one

Similarity: 0.77