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Chemical Structure| 1769-24-0
Chemical Structure| 1769-24-0
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Product Details of [ 1769-24-0 ]

CAS No. :1769-24-0 MDL No. :MFCD05270928
Formula : C9H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :FIEYHAAMDAPVCH-UHFFFAOYSA-N
M.W :160.17 Pubchem ID :135400457
Synonyms :
2-Methylquinazolin-4-ol

Calculated chemistry of [ 1769-24-0 ]

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) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 1.92
Consensus Log Po/w : 1.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.85
Solubility : 0.224 mg/ml ; 0.0014 mol/l
Class : Soluble
Log S (Ali) : -2.83
Solubility : 0.236 mg/ml ; 0.00147 mol/l
Class : 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 : 1.55

Safety of [ 1769-24-0 ]

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 [ 1769-24-0 ]

* 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 [ 1769-24-0 ]
  • Downstream synthetic route of [ 1769-24-0 ]

[ 1769-24-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1769-24-0 ]
  • [ 6484-24-8 ]
YieldReaction ConditionsOperation in experiment
73% for 0.25 h; Microwave irradiation Molecule 37 was prepared in two steps from commercial 2-methylquinazolin-4(3H)-one. This last was first chlorinated at position 4, by using POCl3, according to a previously microwave-assisted reported procedure
[25]
, leading to 4-chloro-2-methylquinazoline in 73percent yield.
Then, the general DMAP-catalyzed operating procedure described in κ 3.1.3.
was applied to this intermediate product, leading to molecule 37 in 45percent yield, as a beige powder.
Mp 118 °C, (isopropanol).
1H NMR (200 MHz, CDCl3) δ = 8.33 (d, J = 8 Hz, 1H), 7.95-7.83 (m, 3H), 7.65-7.56 (m, 2H), 7.42-7.25 (m, 2H), 2.59 (s, 3H), 2.47 (s, 3H).
13C NMR (50 MHz, CDCl3) δ = 197.9, 166.3, 163.7, 152.0, 150.9, 134.3, 133.3, 132.0, 130.1, 127.1, 127.0, 126.0, 123.8, 123.4, 114.3, 30.1, 26.2. LC-MS (ESI+) tR 4.60 min, m/z [M + H]+ 279.19. MW: 278.31 g/mol. Anal. Calcd for C17H14N2O2: C, 73.37; H, 5.07; N, 10.07. Found: C, 73.82; H, 5.11; N, 9.93.
71%
Stage #1: With N,N-diethylaniline In toluene for 0.0833333 h; Heating / reflux
Stage #2: With trichlorophosphate In toluene for 2 h; Heating / reflux
Stage #3: With sodium hydroxide In water; toluene
To a solution of 2-methylquinazolin-4(3H)-one (3.28 g, 20.50 mmol) in toluene (55 mL) was added N,N-diethyl aniline (4.92 mL, 30.74 mmol).
The reaction mixture was stirred was 5 minutes at reflux temperature using a condenser equipped with a CaCl2 drying tube. POCl3 (1.56 mL, 17.01 mmol) was then added and the reaction mixture was refluxed for 2 hours.
The solid was slowly neutralized with a solution of 5percent NaOH in the presence of ice.
The precipitate was filtered and washed with water to yield the desired compound as a yellow solid, 71percent
45% at 120℃; for 3 h; 4-Chloro-2-methyl-quinazoline : A stirred suspension of 2-methyl-4 (3H) - quinazolinone (5 g, 31.2 mmol) in POCI3 (100 mL) was heated at 120°C for 3 h. The excess POC13 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NAHC03, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NACI, dried over anhydrous MGS04, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDC13) : 8.21-8. 25 (m, 1H), 7.89-7. 99 (m, 2H), 7.66 (ddd, 1H, J=1. 8,6. 6,8. 7), 2. 87 (s, 3H).
45% at 120℃; for 3 h; A stirred suspension of 2-methyl-4(3H)- quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 1 2O0C for 3 h. The excess POCl3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCO3, and the mixture was extracted with ettiyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J= 1.8, 6.6, 8.7), 2.87 (s, 3H).
45%
Stage #1: at 120℃; for 3 h;
Stage #2: With sodium hydrogencarbonate In water
A stirred suspension of 2-methy 1-4(3 H)- quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 1200C for 3 h. The excess POCI3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCO3, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J= 1.8, 6.6, 8.7), 2.87 (s, 3H).
45% at 120℃; for 3 h; (4-Methoxy-phenyl)-methyl-(2-methyl-quinazolin-4-yl)-amine hydrochloride[0038] a) 4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methy 1-4(3 H)- quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 1200C for 3 h. The excess POCI3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCψ3, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column <n="14"/>chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J= 1.8, 6.6, 8.7), 2.87 (s, 3H).
45%
Stage #1: at 120℃; for 3 h;
Stage #2: With sodium hydrogencarbonate In waterColling with ice
[0030] a) 4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methyl-4(3H)- quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 1200C for 3 h. The excess POCI3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCψ3, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J= 1.8, 6.6, 8.7), 2.87 (s, 3H).
45%
Stage #1: at 120℃; for 3 h;
Stage #2: With sodium hydrogencarbonate In water at 0℃;
4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methy 1-4(3 H)- quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 1200C for 3 h. The excess POCI3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCψ3, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 <n="12"/>mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J= 1.8, 6.6, 8.7), 2.87 (s, 3H).
45% at 120℃; for 3 h; 4-Chloro-2-methyl-quinazoline: A stirred suspension of 2- methyl-4(3H)-quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 12O0C for 3 h. The excess POCl3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCO3, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was <n="14"/>purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J = 1.8, 6.6, 8.7), 2.87 (s, 3H).
45% at 120℃; for 3 h; 4-Chloro-2-methyl-quinazoline: A stirred suspension of 2-methyl-4(3H)- quinazolinone (5 g, 31.2 mmol) in POCl3 (100 mL) was heated at 1200C for 3 h. The excess POCI3 was removed under vacuum, then to the residue was added crushed ice and 200 mL of saturated NaHCψ3, and the mixture was extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water, saturated NaCl, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by column chromatography (5-8percent ethyl acetate/hexane) to give the title compound (2.5 g, 14.0 mmol, 45percent). 1H NMR (CDCl3): 8.21 - 8.25 (m, IH), 7.89 - 7.99 (m, 2H), 7.66 (ddd, IH, J= 1.8, 6.6, 8.7), 2.87 (s, 3H).
39% With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In toluene for 3 h; Heating / reflux Step-2; 4-Chloro-2-methylquinazoline; To a mixture of 2-methylquinazolin-4(3H)-one (9.2g, 0.0574mol) and phosphorous oxychloride (5.8g, 0.037mol) in dry toluene (250ml) was added N,N-dimethyl aniline (13.9g, 0.14mol) and the mixture was refluxed for 3h. The reaction mixture was cooled and washed with water, brine and dried. The solvent was removed under vacuum and the residue was purified by chromatography (silica gel, 60-120 mesh) eluting with pet ether/ ethyl acetate (9/1) to afford 4g (39percent) of the titled compound as a solid.LCMS: Mass found (M+l, 178.9), 1H NMR (CDCl3 :300MHz) δ 2.86 (3H, s), 7.63-7.68 (IH, m), 7.89-7.98 (2H, m), 8.21-8.24 (IH, m).

Reference: [1] Synthetic Communications, 2011, vol. 41, # 24, p. 3644 - 3653
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 6, p. 840 - 847
[3] MedChemComm, 2013, vol. 5, # 11, p. 1700 - 1707
[4] Tetrahedron, 2014, vol. 70, # 44, p. 8257 - 8266
[5] European Journal of Medicinal Chemistry, 2016, vol. 119, p. 34 - 44
[6] Patent: US2009/23773, 2009, A1, . Location in patent: Page/Page column 65
[7] Canadian Journal of Chemistry, 1984, vol. 62, # 11, p. 2570 - 2577
[8] Synlett, 2001, # 11, p. 1707 - 1710
[9] Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6572 - 6589
[10] Patent: WO2005/3100, 2005, A2, . Location in patent: Page 194
[11] Patent: WO2006/74187, 2006, A2, . Location in patent: Page/Page column 54
[12] Patent: WO2008/124826, 2008, A1, . Location in patent: Page/Page column 12
[13] Patent: WO2008/124822, 2008, A1, . Location in patent: Page/Page column 12-13
[14] Patent: WO2009/23876, 2009, A1, . Location in patent: Page/Page column 9
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[19] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 545 - 548
[20] Synthetic Communications, 2012, vol. 42, # 12, p. 1715 - 1723
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  • [ 1769-24-0 ]
  • [ 6484-24-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2341 - 2351
[2] Patent: WO2005/3100, 2005, A2, . Location in patent: Page 137
[3] Patent: CN106045923, 2016, A, . Location in patent: Paragraph 0344; 0345; 0346; 0347
[4] Patent: US2018/98990, 2018, A1, . Location in patent: Paragraph 0236-0237
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