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[ CAS No. 199678-12-1 ] {[proInfo.proName]}

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Chemical Structure| 199678-12-1
Chemical Structure| 199678-12-1
Structure of 199678-12-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 199678-12-1 ]

CAS No. :199678-12-1 MDL No. :MFCD01318668
Formula : C11H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WNDAEOTYLPWXPN-UHFFFAOYSA-N
M.W : 200.19 Pubchem ID :1514324
Synonyms :

Calculated chemistry of [ 199678-12-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.43
TPSA : 63.08 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 1.39
Log Po/w (WLOGP) : 1.84
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.767 mg/ml ; 0.00383 mol/l
Class : Soluble
Log S (Ali) : -2.32
Solubility : 0.962 mg/ml ; 0.00481 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0567 mg/ml ; 0.000283 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 199678-12-1 ]

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 [ 199678-12-1 ]

* 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 [ 199678-12-1 ]
  • Downstream synthetic route of [ 199678-12-1 ]

[ 199678-12-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 14047-29-1 ]
  • [ 4595-60-2 ]
  • [ 199678-12-1 ]
YieldReaction ConditionsOperation in experiment
89% With sodium carbonate In acetonitrile at 90℃; for 17 h; Example 105 N-(PYRIDIN-3-YLMETHYL)-10-(4-PYRIMIDIN-2-YLBENZOYL)-10,11-DIHYDRO-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-3-CARBOXAMIDE Step A. 4-Pyrimidin-2-ylbenzoic acid; To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 2-bromopyrimidine (0.630 g, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and the mixture was purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (240 mg) was then added and the reaction mixture heated to 90° C. for 17 hours. The hot reaction mixture was filtered through celite and concentrated in vacuo to remove the acetonitrile. The resulting aqueous suspension was washed with dichloromethane (2.x.30 mL) and then acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was diluted with water (20 mL), filtered and the solid product dried in vacuo at 50° C. overnight to give the title compound (0.709 g, 89percent) as a white solid, m.p. 237° C. MS [(+)ESI, m/z]: 201 [M+H]+ MS [(-)ESI, m/z]: 199 [M-H]- Anal. Calcd for C11H8N2O2: C, 66.00; H, 4.03; N, 13.99. Found: C, 65.72; H, 3.87; N, 14.01.
2 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrileInert atmosphere; Reflux To a solution of compound 1 (2g, 12.6mmol) and compound 2 (2.2g, 13.2mmol) in CH3CN, was added 0.5M Na2CO3 (2.7g, 25.2mmol) and the mixture was purged with N2 for 10 mm. Pd(PPh3)4 (800mg) was then added and the mixture heated at reflux overnight. The mixture was filtered, diluted with water and extracted with EA. The resulting aqueous mixture was acidified to pH = 1 and a precipitate formed. The precipitate was filtered and dried to give 2g of compound 3.
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8670 - 8692
[2] Patent: US2006/287522, 2006, A1, . Location in patent: Page/Page column 51
[3] Synlett, 2000, # 6, p. 829 - 831
[4] Patent: WO2016/77232, 2016, A2, . Location in patent: Page/Page column 44; 45
  • 2
  • [ 466634-79-7 ]
  • [ 199678-12-1 ]
YieldReaction ConditionsOperation in experiment
77% With sodium hydroxide In methanol at 20℃; for 2 h; 4-(Pyrimidin-2-yl)benzoic acid (0555) In a 250-mL round-bottom flask were combined the compound from the previous step (4.4 g, 20.54 mmol, 1.00 equiv), NaOH (2.4 g, 60.00 mmol, 2.92 equiv), and methanol (50 mL). The resulting solution was stirred for 2 h at room temperature. The pH value of the solution was adjusted to 7 with HCl (1 M). The solids that formed were collected by filtration, affording 3.15 g (77percent) of the product as a light yellow solid.
Reference: [1] Patent: US2016/237043, 2016, A1, . Location in patent: Paragraph 0553; 0555
  • 3
  • [ 77232-38-3 ]
  • [ 199678-12-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 631 - 634
  • 4
  • [ 99768-12-4 ]
  • [ 199678-12-1 ]
Reference: [1] Patent: US2016/237043, 2016, A1,
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