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Product Details of [ 7142-09-8 ]

CAS No. :7142-09-8 MDL No. :MFCD00195330
Formula : C9H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :VVMQUCPOLAQEBB-UHFFFAOYSA-N
M.W : 194.62 Pubchem ID :135451982
Synonyms :

Calculated chemistry of [ 7142-09-8 ]      Expand+

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 : 52.34
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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 1.8
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.346 mg/ml ; 0.00178 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.812 mg/ml ; 0.00417 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.24
Solubility : 0.0111 mg/ml ; 0.0000573 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 7142-09-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7142-09-8 ]

* 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 [ 7142-09-8 ]
  • Downstream synthetic route of [ 7142-09-8 ]

[ 7142-09-8 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 21739-93-5 ]
  • [ 124-42-5 ]
  • [ 7142-09-8 ]
YieldReaction ConditionsOperation in experiment
81% With copper(l) iodide; TPGS-450-M; caesium carbonate In water at 20℃; for 12 h; Inert atmosphere; Green chemistry General procedure: A two-neck round bottom flask was charged with a magnetic stirrer, evacuated and backfilled with nitrogen. Substituted 2-halobenzoic acid (1, 0.5 mmol) and amidine hydrochloride (2, 0.75 mmol) or bis(guanidine) sulphate (2, 0.38 mmol) in 2 wt percent TPGS-750-M (3 mL) were added under nitrogen atmosphere. After a 10-min stirring, Cs2CO3 (1 mmol, 326 mg) was added to the flask. 15 min later, CuI (0.1 mmol, 19 mg) was added to the flask. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for 12 h (see Table 3 in text). After completion of the reaction, the mixture was extracted with EtOAc (1 mL), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1 to 1:1) as eluent to provide the desired product.
Reference: [1] RSC Advances, 2014, vol. 4, # 91, p. 50285 - 50294
[2] Angewandte Chemie - International Edition, 2009, vol. 48, # 2, p. 348 - 351
[3] Tetrahedron, 2015, vol. 71, # 29, p. 4853 - 4858
[4] Applied Organometallic Chemistry, 2014, vol. 28, # 9, p. 661 - 665
  • 2
  • [ 78-39-7 ]
  • [ 5202-85-7 ]
  • [ 7142-09-8 ]
YieldReaction ConditionsOperation in experiment
92% With acetic acid In ethanol at 110℃; for 24 h; Inert atmosphere; Sealed tube General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2–3 equiv) and absolute ethanol (2–3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12–72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:
Reference: [1] Molecules, 2018, vol. 23, # 11,
  • 3
  • [ 7033-50-3 ]
  • [ 7142-09-8 ]
YieldReaction ConditionsOperation in experiment
82.7% at 130℃; for 7 h; General procedure: A solution of corresponding 2-methyl-4H-benzo[d][1,3]oxazin-4-one (16a-b) (1 mmol) in formamide (15 mL) was heated to 130 °C for 7 h (monitored by TLC & LCMS for completion). Upon cooling, the mixture got solidified, which was further washed with water, and recrystallized from ethanol to give 2-methylquinazolin-4(3H)-one (17a-b).
77% at 20℃; 6-chloro-2-methylquinazolin-4(3H)-one 10 g (58 mmol) 2-amino-5-chlorobenzoic acid was solved in 35 ml acetic anhydride and was stirred at reflux temperature for 4 hours. The reaction mixture was cooled down to room temperature and the solvent was rotary evaporated. The crude product was washed with hexane/ether 2:1 and than filtered. The solid 6-chloro-2-methyl-4H-3,1-benzoxazin-4-one (58 mmol) was suspended in 80 ml concentrated ammonium hydroxide and stirred at room temperature overnight. 10 percent sodium hydoxide solution was given to the reaction mixture resulting a transparent solution. The pH was adjusted to 7 with acetic acid. The product, which was precipitated from the solution, was filtered, washed with water and dried under vacuum overnight. Preparation of other 2-methylquinazolin-4(3H)-one derivatives were carried out with the same method. Yield: 8.76 g (77 percent) 1H NMR (300 MHz, DMSO-d6) δ ppm 7.98 (s, 1H); 7,76 (6Hz, d, 1H); 7.57 (9 Hz, d, 1H); 2.34 (s, 3H). LC-MS (ESI): m z (M+H)+ 195, Rt: 2.43 min.
Reference: [1] Farmaco, 1999, vol. 54, # 11-12, p. 780 - 784
[2] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 613 - 627
[3] Patent: WO2015/19121, 2015, A1, . Location in patent: Page/Page column 8
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1721 - 1728
  • 4
  • [ 123-54-6 ]
  • [ 5202-85-7 ]
  • [ 7142-09-8 ]
YieldReaction ConditionsOperation in experiment
81% With ytterbium(III) triflate In 1,3,5-trimethyl-benzene at 60℃; for 24 h; Inert atmosphere General procedure: 2-aminobenzamide (1, 1.0 mmol), 1,3-diketone (2, 1.5 mmol), Yb(OTf)3 (0.050 mmol, 5.0 molpercent),and mesitylene (2.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 60°C (bath temp.) for 24 h with stirring. The reaction mixture was then cooled to room temperature and analyzed by GLCand GC-MS. The product 3 was isolated by medium-pressure column chromatography on silica gel(eluent: EtOAc/hexane = 30/70 ~ EtOAc 100percent. For 3j, eluent: MeOH/CHCl3 = 30/70 ~ 50/50) andrecrystallization from MeOH/hexane. The products 3l and 3m were isolated by recrystallizationfrom EtOAc/hexane. 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6 (For 3j, in a mixture of DMSO-d6 and methanol-d4). Elemental analyses were performed at the Microanalytical Center of Kyoto University. The analytical and spectral data of 3a,10 3b-c,11 3d,12 3e,13 3f,14 3g-h,10 and 3j-l,7 are fully consistent with those reported previously. The products 3i,15 and 3m16 were characterized below.
Reference: [1] Heterocycles, 2016, vol. 93, # 2, p. 816 - 823
[2] RSC Advances, 2015, vol. 5, # 104, p. 85646 - 85651
  • 5
  • [ 27007-53-0 ]
  • [ 124-42-5 ]
  • [ 7142-09-8 ]
Reference: [1] Chemical Communications, 2008, # 47, p. 6333 - 6335
  • 6
  • [ 108-24-7 ]
  • [ 635-21-2 ]
  • [ 7142-09-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 119 - 132
  • 7
  • [ 13421-00-6 ]
  • [ 124-42-5 ]
  • [ 7142-09-8 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 11, p. 1881 - 1888
  • 8
  • [ 64-17-5 ]
  • [ 5202-85-7 ]
  • [ 7142-09-8 ]
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 21, p. 2099 - 2102
  • 9
  • [ 635-21-2 ]
  • [ 75-05-8 ]
  • [ 7142-09-8 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 31, p. 4362 - 4365
  • 10
  • [ 635-21-2 ]
  • [ 7142-09-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1721 - 1728
[2] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 613 - 627
[3] Patent: WO2015/19121, 2015, A1,
  • 11
  • [ 7033-53-6 ]
  • [ 7142-09-8 ]
  • [ 5202-87-9 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2423
  • 12
  • [ 5202-87-9 ]
  • [ 7142-09-8 ]
Reference: [1] Farmaco, 1999, vol. 54, # 11-12, p. 780 - 784
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