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[ CAS No. 19213-72-0 ] {[proInfo.proName]}

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Chemical Structure| 19213-72-0
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Product Details of [ 19213-72-0 ]

CAS No. :19213-72-0 MDL No. :MFCD00014498
Formula : C6H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YICRPEGTQDSFEX-UHFFFAOYSA-N
M.W : 140.14 Pubchem ID :87963
Synonyms :

Calculated chemistry of [ 19213-72-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.78
TPSA : 44.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 0.43
Log Po/w (WLOGP) : 0.89
Log Po/w (MLOGP) : -0.43
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 0.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.15
Solubility : 9.88 mg/ml ; 0.0705 mol/l
Class : Very soluble
Log S (Ali) : -0.92
Solubility : 16.7 mg/ml ; 0.119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.86
Solubility : 19.2 mg/ml ; 0.137 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 19213-72-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19213-72-0 ]

* 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 [ 19213-72-0 ]
  • Downstream synthetic route of [ 19213-72-0 ]

[ 19213-72-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 19213-72-0 ]
  • [ 16042-25-4 ]
Reference: [1] Patent: US5023336, 1991, A,
  • 2
  • [ 288-32-4 ]
  • [ 541-41-3 ]
  • [ 19213-72-0 ]
YieldReaction ConditionsOperation in experiment
17% at 0 - 20℃; for 5 h; Imidazole is added to the reactor (3.75g, 55 . 0mmol), thf (50.0 ml), the reaction is cooled to 0 °C, the ethyl chloroformate (2.58 ml, 27 . 0mmol) dropwise wherein the 0 °C stirring 1h rear, moving to the room temperature, reaction 4h. Filtering the reaction liquid, turns on lathe does, its re-dissolved in 100 ml diethyl ether, washed with water, drying by anhydrous magnesium sulphate the organic phase, the turns on lathe does colorless liquid, i.e. compound 3 (1.28g, 17percent yield)
17% at 0 - 20℃; for 5 h; Imidazole is added to the reactor (3.75g, 55 . 0mmol), thf (50.0 ml), the reaction is cooled to 0 °C, the ethyl chloroformate (2.58 ml, 27 . 0mmol) dropwise wherein the 0 °C stirring 1h rear, moving to the room temperature, reaction 4h. Filtering the reaction liquid, turns on lathe does, its re-dissolved in 100 ml diethyl ether, washed with water, drying by anhydrous magnesium sulphate the organic phase, the turns on lathe does colorless liquid, i.e. compound 3 (1.28g, 17percent yield);
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 33, p. 8304 - 8308
[2] Organic Letters, 2010, vol. 12, # 20, p. 4572 - 4575
[3] Patent: CN105566347, 2016, A, . Location in patent: Paragraph 0033; 0034; 0035
[4] Patent: CN105503932, 2016, A, . Location in patent: Paragraph 0045; 0046; 0047
[5] Justus Liebigs Annalen der Chemie, 1957, vol. 609, p. 75,82
[6] Tetrahedron Letters, 1982, vol. 23, # 20, p. 2113 - 2116
[7] Journal of Organic Chemistry, 1982, vol. 47, # 21, p. 4040 - 4045
[8] Tetrahedron, 2011, vol. 67, # 46, p. 8851 - 8859
[9] Tetrahedron Letters, 2012, vol. 53, # 9, p. 1060 - 1062
  • 3
  • [ 64-17-5 ]
  • [ 530-62-1 ]
  • [ 19213-72-0 ]
Reference: [1] Nucleosides and Nucleotides, 1999, vol. 18, # 9, p. 2109 - 2120
[2] Tetrahedron Letters, 1982, vol. 23, # 20, p. 2113 - 2116
[3] Gazzetta Chimica Italiana, 1993, vol. 123, # 10, p. 559 - 562
[4] Green Chemistry, 2012, vol. 14, # 2, p. 326 - 329
[5] Tetrahedron Letters, 2012, vol. 53, # 19, p. 2373 - 2376
  • 4
  • [ 288-32-4 ]
  • [ 63436-79-3 ]
  • [ 19213-72-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 22, p. 4519 - 4522
  • 5
  • [ 288-32-4 ]
  • [ 74877-64-8 ]
  • [ 19213-72-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 22, p. 4519 - 4522
  • 6
  • [ 64-17-5 ]
  • [ 530-62-1 ]
  • [ 288-32-4 ]
  • [ 19213-72-0 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 1, p. 23 - 30
[2] Russian Journal of Applied Chemistry, 2012, vol. 85, # 3, p. 456 - 459
  • 7
  • [ 110-85-0 ]
  • [ 19213-72-0 ]
  • [ 142-64-3 ]
  • [ 120-43-4 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 2, p. 326 - 329
  • 8
  • [ 19213-72-0 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 103, p. 59594 - 59602
  • 9
  • [ 19213-72-0 ]
  • [ 93-10-7 ]
  • [ 4491-33-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 8, p. 1970 - 1973
  • 10
  • [ 19213-72-0 ]
  • [ 87-51-4 ]
  • [ 778-82-5 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 8, p. 1970 - 1973
  • 11
  • [ 19213-72-0 ]
  • [ 1878-68-8 ]
  • [ 14062-25-0 ]
YieldReaction ConditionsOperation in experiment
89% at 80℃; for 24 h; Inert atmosphere; Sealed vial General procedure: Carboxylic acid (0.5 mmol) and MImC (2a, 1.0 mmol) were placed in a dry 20 mL vial with a Teflon tape-coated thread. A magnetic stirbar was added, followed by dry MeCN (1.0 mL), and the vial was quickly sealed with a plastic cap (gas is evolved during the course of the reaction. All experiments should be performed behind a blast shield if a sealed container is used.). The reaction mixture was then stirred at 23 °C for 15 min and then heated to 80 °C using a heating block for 24 h. The mixture was cooled to room temperature and then the vial was carefully opened (CAUTION: vial under pressure.). The volatiles were removed in vacuo, the resulting residue was dissolved in diethyl ether (20 mL), and then washed with 1 M HCl (10 mL). The aqueous layer was back-extracted with diethyl ether (20 mL) and the organic fractions were combined, washed with a saturated solution of NaHCO3 and then brine, dried over MgSO4, and concentrated in vacuo to afford the desired ester.
Reference: [1] Tetrahedron, 2011, vol. 67, # 46, p. 8851 - 8859
[2] Organic Letters, 2012, vol. 14, # 8, p. 1970 - 1973
  • 12
  • [ 19213-72-0 ]
  • [ 14062-24-9 ]
  • [ 19677-37-3 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5 h;
Stage #2: at -78 - 20℃;
General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 °C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 °C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4percent ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81percent yield) as a colorless liquid.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 9, p. 1060 - 1062
  • 13
  • [ 19213-72-0 ]
  • [ 2749-11-3 ]
  • [ 4042-35-7 ]
Reference: [1] Chemistry Letters, 2013, vol. 42, # 2, p. 109 - 111
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