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[ CAS No. 499195-60-7 ] {[proInfo.proName]}

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Chemical Structure| 499195-60-7
Chemical Structure| 499195-60-7
Structure of 499195-60-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 499195-60-7 ]

CAS No. :499195-60-7 MDL No. :MFCD09861393
Formula : C13H11ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PTSZMMLYAGLVQJ-UHFFFAOYSA-N
M.W : 262.69 Pubchem ID :11065261
Synonyms :

Calculated chemistry of [ 499195-60-7 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.15
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.56
TPSA : 52.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.85
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.97
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 3.31
Consensus Log Po/w : 2.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.0631 mg/ml ; 0.00024 mol/l
Class : Soluble
Log S (Ali) : -3.81
Solubility : 0.0407 mg/ml ; 0.000155 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.27
Solubility : 0.00141 mg/ml ; 0.00000538 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.09

Safety of [ 499195-60-7 ]

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 [ 499195-60-7 ]

* 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 [ 499195-60-7 ]
  • Downstream synthetic route of [ 499195-60-7 ]

[ 499195-60-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 3934-20-1 ]
  • [ 4334-88-7 ]
  • [ 499195-60-7 ]
YieldReaction ConditionsOperation in experiment
60% With sodium carbonate In toluene at 75 - 100℃; Example 1 - Synthesis of Compound 3; A mixture of 4-ethoxycarbonylphenyl boronic acid (23.11 g, 119 mmol), 2,4- dichloropyrimidine (16.90 g, 113 mmol), toluene (230 mL) and aqueous sodium carbonate (2 M, 56 mL) was stirred vigorously and nitrogen was bubbled through the suspension for 15 minutes. Tetrakis(triphenylphosphine)palladium[0] (2.61 g, 2.26 mmol) was added. Nitrogen was bubbled through for another 10 min., the mixture was heated to 100°C, then at 75°C overnight. The mixture was cooled, diluted with ethyl acetate (200 mL), water (100 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (100 ml) and the two organic extracts were combined. The organics were washed with brine, filtered through sodium sulfate, <n="58"/>concentrated, and the resultant solid was triturated with methanol (100 niL) and filtered. The solids were washed with methanol (2 x 30 mL) and air dried. This material was dissolved in acetonitrile (150 mL) and dichloromethane (200 mL), stirred with MP.TMT Pd-scavenging resin (Agronaut part number 800471) (7.5 g) over 2 days. The solution was filtered, the solids were washed with dichloromethane (2 x 100 mL), and the filtrate concentrated to give ethyl 4-(2-chloropyrimidin-4-yl)benzoate as anoff-white solid (17.73 g, 60percent) - additional washing with dichloromethane yielded a further 1.38 g and 0.5 g of product. 1H NMR (300 MHz, J6-DMSO) δ 8.89 (IH, d, J= 5.0 Hz); 8.32 (2H, d, J= 8.7 Hz); 8.22 (IH, d, J= 5.5 Hz); 8.12 (2H, d, J= 8.7 Hz); 4.35 (2H, q, J= 7.1 Hz); 1.34 (3H, t, J= 7.1 Hz); LC-ESI-MS (method B): rt 7.3 min.; m/z 263.0 / 265.0 [M+H]+.
37%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃; for 1 h;
Stage #2: at 90℃; for 0.5 h;
Stage #3: With potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 90℃; for 0.5 h;
Ester 1 : Preparation of Ethyl 4-(2-chloropyrimidin-4-yl)benzoate. To a solution of 2,4-dichloropyrimidine [70 g, 470 mmol] in DMF [600 mL] was added (PPh3)2PdCl2 [9.9 g, 14 mmol] and mixture was heated to 90°C for 1 h. To this, (4-(ethoxycarbonyl)phenyl)boronic acid [91 g, 470 mmol] was added and mixture was heated to 90°C for additional 0.5 h. A solution of potassium bicarbonate [282 g, 2.8 mol] in 200 mL of water was added to reaction mixture and stirred for 0.5 h at 90°C. After completion of reaction, mixture was quanched in ice cooled water [500 mL]. The off white solid obtained was filtered, washed with water and dried under vacuum to get title compound. [45 g, 37percent].
Reference: [1] Patent: WO2008/109943, 2008, A1, . Location in patent: Page/Page column 56-57
[2] Patent: WO2015/19365, 2015, A1, . Location in patent: Page/Page column 17; 18
  • 2
  • [ 68-12-2 ]
  • [ 499195-60-7 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 19, p. 3011 - 3018
  • 3
  • [ 499195-60-7 ]
  • [ 1056634-68-4 ]
Reference: [1] Patent: WO2008/109943, 2008, A1,
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