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[ CAS No. 604-50-2 ] {[proInfo.proName]}

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Chemical Structure| 604-50-2
Chemical Structure| 604-50-2
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Product Details of [ 604-50-2 ]

CAS No. :604-50-2 MDL No. :MFCD00731030
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RWFOOMQYIRITHL-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :11788
Synonyms :

Calculated chemistry of [ 604-50-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.09
TPSA : 54.86 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) : -7.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 0.31
Log Po/w (WLOGP) : 0.23
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 1.61
Consensus Log Po/w : 0.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 3.54 mg/ml ; 0.0201 mol/l
Class : Very soluble
Log S (Ali) : -1.02
Solubility : 16.6 mg/ml ; 0.0944 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.7
Solubility : 0.351 mg/ml ; 0.00199 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 604-50-2 ]

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 [ 604-50-2 ]

* 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 [ 604-50-2 ]
  • Downstream synthetic route of [ 604-50-2 ]

[ 604-50-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 119-68-6 ]
  • [ 917-61-3 ]
  • [ 604-50-2 ]
YieldReaction ConditionsOperation in experiment
84% With acetic acid; sodium hydroxide In water at 75℃; for 4 h; Sodium cyanate (28mmol) in water (25mL) was added to a solution of N-methyl anthranilic acid (20mmol) and acetic acid (0.2mL) in water (50mL) with stirring. When the temperature of the reaction mixture reached 40°C, NaOH was added in portions till the reaction temperature reach to 75°C. Stirring was continued without cooling for 4h, after which the crystals were filtered off and dissolved in boiling water (50mL). The solution was acidified with 50percent H2SO4 to pH 1–2. The precipitated crystals were filtered off, washed with water and recrystallized from 50percent acetic acid to give compound 2 (2.92g, 84percent); m p 278°C [24].
77%
Stage #1: With acetic acid In water at 50℃; for 1 h;
Stage #2: at 50 - 80℃;
Sodium cyanate (30.15 g, 0.46 mol) was added to a slurry of N- methylanthranilic acid (50.0 g, 0.33 mol) in water (1 .75 L) and acetic acid (3.3 mL). The reaction mixture was heated to 50 °C for 1 h. The solution was slowly basified by the addition of sodium hydroxide (exothermic). The resulting solution was heated to 80 °C and stirred overnight. The reaction mixture was cooled to 0 °C and the resultant precipitate collected by filtration. The solid was dissolved in boiling water (200 mL) and acidified with cone, sulfuric acid to pH 2. The slurry was cooled to room temperature and filtered. The solid was dried in a vacuum oven to give 1 -methylquinazoline-2,4(1 H,3H)-dione (53 g, 0.30 mol, 77percent).1 H NMR (300MHz, DMSO-d6) δ = 1 1 .54 (br. s., 1 H), 8.00 (d, J = 7.7 Hz, 1 H), 7.77 (t, J = 7.9 Hz, 1 H), 7.43 (d, J = 8.6 Hz, 1 H), 7.28 (t, J = 7.5 Hz, 1 H), 3.33 (s, 3H)
69% With acetic acid; sodium hydroxide In water at 40 - 75℃; for 4 h; 2-(Methylamino)benzoic acid (4.50 g, 0.0300 mol) and acetic acid (0.3 mL) were dissolved in water (158 mL), a solution of sodium isocyanate (2.76 g, 42.0 mmol) in water (54 mL) was added slowly at room temperature.
The reaction mixture was heated to 40°C and added with sodium hydroxide (34.8 g, 0.870 mol).
The temperature was raised to 75°C and the reaction solution was stirred for 4 hours, cooled to room temperature, filtered and the filter cake was dissolved in boiling water (10 mL).
The system was adjusted to pH 1-2 with 50percent sulfuric acid solution (15 mL), filtered and the filter cake was washed with a small amount of water (3 mL) and dried under reduced pressure to give 1-methylquinazoline-2,4-dione (3.64 g, as a yellow solid) with a yield of 69percent. 1H NMR: (400 MHz, DMSO-d6) δ 11.55(s, 1H), 8.00(d, J = 8.0 Hz, 1H), 7.78(t, J = 8.0 Hz, 1H), 7.42(d, J = 8.0 Hz, 1H), 7.28(t, J = 8.0 Hz, 1H), 3.44(s, 3H). MS-ESI calcd. [M + H]+ 177, found 177.
Reference: [1] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 12, p. 1508 - 1514
[2] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 110, p. 324 - 332
[3] Patent: WO2016/92326, 2016, A1, . Location in patent: Page/Page column 97; 113
[4] Patent: EP3299371, 2018, A1, . Location in patent: Paragraph 0525; 0526
[5] Letters in Drug Design and Discovery, 2014, vol. 11, # 6, p. 712 - 720
  • 2
  • [ 590-28-3 ]
  • [ 85-91-6 ]
  • [ 604-50-2 ]
YieldReaction ConditionsOperation in experiment
80% With acetic acid In water at 20 - 70℃; To a stirred mixture of Methyl /V-Methyl anthranilate (1 .46 mL, 10 mmol) in glacial acetic acid (10 mL) was added KOCN (975 mg, 12 mmol) in 3 mL of H20. The solution was stirred at room temperature overnight and then heated to 70°C for 3 hours. The reaction was cooled to 0°C and then filtered. The white solid was washed with cold ethanol and dried. The product was collected as a white solid (1 .46g) in 80percent yield. 1 H NMR (300 MHz, DMSO-d6) δ 1 1 .53 (br. s., 1 H), 7.97 (d, J = 7.71 Hz, 1 H), 7.88-7.64 (m, 1 H), 7.38 (d, J = 8.81 Hz, 1 H), 7.25 (t, J = 7.57 Hz, 1 H) 3.42 (s, 3H).
Reference: [1] Patent: WO2016/19312, 2016, A2, . Location in patent: Paragraph 0450-0451
  • 3
  • [ 119-68-6 ]
  • [ 57-13-6 ]
  • [ 604-50-2 ]
YieldReaction ConditionsOperation in experiment
64.3% at 150℃; for 5 h; Urea (460 mmol) was heated to melt, then 2-methylaminobenzoic acid (46 mmol) was added.
The mixture was stirred for 5 h at 150 °C and then cooled to below 100 °C. Water (70 mL) was added to quench the reaction.
The precipitated was collected and recrystallized in a mixed solution of acetone (10 mL) and water (100 mL) to afford compound 1 as a white powder (5.25 g, 64.3percent); mp 278-279 °C; 1H NMR (DMSO-d6) δ (ppm): 3.43 (s, 3H), 7.26 (t, J = 12 Hz, 1H), 7.41 (d, J = 12 Hz, 1H), 7.75 (t, J = 15 Hz, 1H), 7.98 (d, J = 6 Hz, 1H), 11.54 (s, 1H). ESI-MS (m/z): 177 (M+H)+.
Reference: [1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2169 - 2177
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 13, p. 3405 - 3413
[4] Yakugaku Zasshi, 1916, # 417, p. 17[5] Chem.Abstr., 1917, vol. 11, p. 578
[6] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 560 - 569
  • 4
  • [ 590-28-3 ]
  • [ 119-68-6 ]
  • [ 604-50-2 ]
Reference: [1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 6, p. 708 - 711
[3] Yakugaku Zasshi, 1916, # 417, p. 17[4] Chem.Abstr., 1917, vol. 11, p. 578
  • 5
  • [ 7505-81-9 ]
  • [ 541-41-3 ]
  • [ 604-50-2 ]
Reference: [1] Organic Mass Spectrometry, 1988, vol. 23, p. 816 - 820
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 2459,2461
  • 6
  • [ 10328-92-4 ]
  • [ 604-50-2 ]
Reference: [1] Organic Mass Spectrometry, 1988, vol. 23, p. 816 - 820
  • 7
  • [ 85-91-6 ]
  • [ 604-50-2 ]
Reference: [1] Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2169 - 2177
  • 8
  • [ 134-20-3 ]
  • [ 604-50-2 ]
Reference: [1] Medicinal Chemistry Research, 2014, vol. 23, # 5, p. 2169 - 2177
  • 9
  • [ 7505-81-9 ]
  • [ 57-13-6 ]
  • [ 604-50-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 39, p. 142
  • 10
  • [ 77-78-1 ]
  • [ 607-19-2 ]
  • [ 604-50-2 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 6, p. 708 - 711
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