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[ CAS No. 94-02-0 ] {[proInfo.proName]}

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Chemical Structure| 94-02-0
Chemical Structure| 94-02-0
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Product Details of [ 94-02-0 ]

CAS No. :94-02-0 MDL No. :MFCD00009196
Formula : C11H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :GKKZMYDNDDMXSE-UHFFFAOYSA-N
M.W : 192.21 Pubchem ID :7170
Synonyms :

Calculated chemistry of [ 94-02-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.34
TPSA : 43.37 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) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.61
Log Po/w (SILICOS-IT) : 2.3
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.22 mg/ml ; 0.00635 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.761 mg/ml ; 0.00396 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.112 mg/ml ; 0.000582 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 94-02-0 ]

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 [ 94-02-0 ]

* 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 [ 94-02-0 ]
  • Downstream synthetic route of [ 94-02-0 ]

[ 94-02-0 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 94-02-0 ]
  • [ 56741-94-7 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: for 1 h; Heating / reflux
Stage #2: at 45℃; Heating / reflux
Intermediate 1A : Preparation of 4-chloro-6-phenylpyrimidin-2-amine; A suspension of guanidine carbonate (3.60 g, 20 mmol) in ethanol (120 mL) and toluene (20 mL) was refluxed under nitrogen for 1 h, during which time about 50 mL of solvent was removed by distillation. After the mixture was cooled to 45 °C, ethyl 3-oxo-3- phenylpropanoate (7.68 g, 40 mmol) was added and the solution was heated at reflux overnight. The desired product precipitated as a white solid during the reaction. Water (50 mL) was added to the reaction and the mixture was refluxed for an additional 30 min. After cooling to rt, the mixture was neutralized with 1N HC1 and placed in the refrigerator for 6 h. The solid was filtered, washed with water followed by ether and dried at 60 °C under vacuum to give the product as white solid (6.45 g, 86percent). MS ES: 188 (M+H) +, calcd 188; RT = 0.91 min; TLC (CH2C12/2M NH3 in MeOH 95/5) Rf = 0.10. A mixture of the above product (6.0 g, 32 mmol) and POC13 (100 mL) was heated at reflux for 1 h. The majority of the POC13 was removed in vacuo and the residue was diluted with EtOAc and poured over an ice/saturated NaHC03 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2SO4), and concentrated. The crude organic concentrate was re-crystallized from EtOAc/ether to give the product 1A as an off-white powder (2. 8 g, 43percent). MS ES: 206 (M+H) +, calcd 206; RT = 2.49 min; TLC (CH2C12/2M NH3 in MeOH 95/5) Rf = 0.72. (Reference 1: H. L. Skulnick, S. D. Weed, E. E. Edison, H. E. Renis, W. Wierenga, and D. A. Stringfellow, J ; Med. Cllem. 1985, 28,1854-1869).
Reference: [1] Patent: WO2005/35507, 2005, A2, . Location in patent: Page/Page column 52
  • 2
  • [ 593-85-1 ]
  • [ 94-02-0 ]
  • [ 56741-94-7 ]
YieldReaction ConditionsOperation in experiment
70% at 80℃; Inert atmosphere General procedure: To a suspension of guanidine carbonate (1.5-5 eq) in ethanol (2 mL/mmol) was added γ-aryl-β-ketoester (1.43-26.6 mmol), and the reaction mixture heated at 80 °C for 15-64 h. Followingreaction completion by TLC, the mixture was cooled to ambient temperature, filtered and thesolid triturated with water (5-20 mL) and acetone (5-20 mL) to give the title compound.
Reference: [1] Tetrahedron, 2015, vol. 71, # 39, p. 7339 - 7343
[2] Journal of the American Chemical Society, 1998, vol. 120, # 27, p. 6761 - 6769
[3] Justus Liebigs Annalen der Chemie, 1891, vol. 262, p. 365
[4] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 203
  • 3
  • [ 50-01-1 ]
  • [ 94-02-0 ]
  • [ 56741-94-7 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 29, p. 15087 - 15090
  • 4
  • [ 124-46-9 ]
  • [ 94-02-0 ]
  • [ 56741-94-7 ]
Reference: [1] Patent: US2001/27196, 2001, A1,
  • 5
  • [ 593-84-0 ]
  • [ 94-02-0 ]
  • [ 56741-94-7 ]
Reference: [1] Journal of the American Chemical Society, 1914, vol. 36, p. 1205
  • 6
  • [ 94-02-0 ]
  • [ 113-00-8 ]
  • [ 56741-94-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 237 - 239
[2] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1864 - 1869
  • 7
  • [ 94-02-0 ]
  • [ 17356-08-0 ]
  • [ 36822-11-4 ]
YieldReaction ConditionsOperation in experiment
24% With sodium ethanolate In ethanolReflux To a solution of compound 12.1 (2 g, 10.41 mmol) in EtOH (15 mL) was added EtONa (7 mL, 18.7 mmol) and compound 1.2 (1.18 g, 15.61 mmol). Stirring was continued at reflux overnight. The solvent was removed under reduced pressure. The reaction was taken up with water, acidified to pH 3, extracted with EtOAc (3 x 20 mL) washed with brine and dried over Na2SO4.The crude was purified by flash chromatography, eluting with CH2C12/MeOH (2.5percent for product) affording the title compound 12.2 (500 mg, 2.44 mmol) as white solid. Yield 24percent.
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999, vol. 54, # 6, p. 788 - 798
[2] Synthetic Communications, 2002, vol. 32, # 6, p. 851 - 855
[3] Patent: WO2016/30534, 2016, A1, . Location in patent: Page/Page column 109
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 745 - 759
[5] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 203
[6] Journal of the American Chemical Society, 1915, vol. 37, p. 381
[7] European Journal of Medicinal Chemistry, 1988, vol. 23, # 1, p. 53 - 62
[8] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1499 - 1504
[9] Journal of Medicinal Chemistry, 1997, vol. 40, # 10, p. 1447 - 1454
[10] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 8, p. 2530 - 2535
[11] European Journal of Medicinal Chemistry, 2014, vol. 80, p. 569 - 578
  • 8
  • [ 1147550-11-5 ]
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  • [ 36822-11-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 203
  • 9
  • [ 3950-02-5 ]
  • [ 94-02-0 ]
  • [ 5556-20-7 ]
  • [ 1190582-62-7 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 2009, vol. 184, # 5, p. 1115 - 1123
  • 10
  • [ 94-02-0 ]
  • [ 26964-24-9 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 9, p. 2511 - 2517
[2] Heterocycles, 1986, vol. 24, # 9, p. 2511 - 2517
  • 11
  • [ 94-02-0 ]
  • [ 98700-53-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 6, p. 1669 - 1675
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 18, p. 3810 - 3815
[3] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 146 - 161
  • 12
  • [ 94-02-0 ]
  • [ 87-66-1 ]
  • [ 38183-03-8 ]
Reference: [1] J. Maharaja Sayajirao Univ. Baroda, 1955, vol. 4, # 2, p. 1,3, 5
  • 13
  • [ 94-02-0 ]
  • [ 3356-89-6 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 127 - 134
  • 14
  • [ 94-02-0 ]
  • [ 56741-95-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1864 - 1869
[2] Tetrahedron, 2015, vol. 71, # 39, p. 7339 - 7343
  • 15
  • [ 94-02-0 ]
  • [ 2881-85-8 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 6, p. 665 - 671
  • 16
  • [ 94-02-0 ]
  • [ 29976-82-7 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 9, p. 2511 - 2517
  • 17
  • [ 94-02-0 ]
  • [ 74-89-5 ]
  • [ 197852-01-0 ]
Reference: [1] Chem. Zentralbl., 1904, vol. 75, # II, p. 905
[2] Chem. Zentralbl., 1904, vol. 75, # II, p. 905
[3] Chem. Zentralbl., 1904, vol. 75, # II, p. 905
  • 18
  • [ 94-02-0 ]
  • [ 127958-10-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6756 - 6761
  • 19
  • [ 94-02-0 ]
  • [ 7063-21-0 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 37, p. 12872 - 12875
[2] Patent: WO2010/120232, 2010, A1, . Location in patent: Page/Page column 74
  • 20
  • [ 94-02-0 ]
  • [ 170564-98-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 7, p. 1042 - 1047
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 7, p. 1042 - 1047
  • 21
  • [ 94-02-0 ]
  • [ 851789-43-0 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 5, p. 918 - 921
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