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[ CAS No. 85363-04-8 ] {[proInfo.proName]}

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Chemical Structure| 85363-04-8
Chemical Structure| 85363-04-8
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Product Details of [ 85363-04-8 ]

CAS No. :85363-04-8 MDL No. :MFCD00239390
Formula : C7H12N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SMZKPZXYDDZDJG-UHFFFAOYSA-N
M.W :156.18 Pubchem ID :545844
Synonyms :

Calculated chemistry of [ 85363-04-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.03
TPSA : 62.12 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) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 0.72
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 0.19
Log Po/w (SILICOS-IT) : 0.1
Consensus Log Po/w : 0.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.0
Solubility : 15.7 mg/ml ; 0.1 mol/l
Class : Very soluble
Log S (Ali) : -1.6
Solubility : 3.9 mg/ml ; 0.025 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.31
Solubility : 7.68 mg/ml ; 0.0492 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 85363-04-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85363-04-8 ]

* 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 [ 85363-04-8 ]
  • Downstream synthetic route of [ 85363-04-8 ]

[ 85363-04-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 24424-99-5 ]
  • [ 151-63-3 ]
  • [ 85363-04-8 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane at 60℃; Sealed tube A 2-acylamidoacetonitrile was prepared similarly at room temperature, using an acid chloride as a starting compound. To a solution of the compound thus obtained (3 mmol) in dry methanol (50 mL) at room temperature under N2 atmosphere was added L-cysteine methyl ester hydrochloride (770 mg, 4.5 mmol) and triethylamine (0.63 mL, 4.5 mmol). The resulting mixture was stirred for 3 h and evaporated to dryness. The residue was taken up in CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic extract was dried over sodium sulfate, filtered, evaporated, and purified by column chromatography (silica gel, hexane/ethyl acetate, 5:1) to give a methyl ester of compounds 14 – 17. Precooled LiOH (0.9 mL, 1 N, 0.9 mmol) was added to the methyl ester (1.0 mmol) in methanol (5 mL) at 0 oC. The suspension was stirred for 1 h at room temperature, diluted with acetone (20 mL) to precipitate the product. The white powder was filtered and dried to give compounds 14 – 17.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6229 - 6232
[2] Chemistry - A European Journal, 2018, vol. 24, # 68, p. 18075 - 18081
  • 2
  • [ 24424-99-5 ]
  • [ 6011-14-9 ]
  • [ 85363-04-8 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydrogencarbonate In tetrahydrofuran; water at 25 - 30℃; To a solution of hydrochloride salt of amino acetonitrile (50 g 487 mmol) dissolved in water (250 ml) and tetrahydrofuran (250 ml) was added sodium bicarbonate (90.14 g, 1073 mmol) under stirring at 25-30 °C. To this was added di- ie/t-butyldicarbonate (117 g, 536 mmol) drop-wise using addition funnel. The progress of reaction was monitored by thin layer chromatography using a mixture of hexane and acetone as solvent. After complete consumption of starting material, ethyl acetate (500 ml) was added to it and organic layer was separated. The aqueous layer was re-extracted with ethyl acetate (1x250 ml). The organic extracts were combined and dried over anhydrous sodium sulfate, then concentrated to yield 66 g of tert-butyl (cyanomethyl)carbamate as a thick liquid in 86percent yield
66% With triethylamine In dichloromethane for 16 h; Reflux Step a:
Aminoacetonitrile hydrochloride (5 g, 54 mmol) was added to dichloromethane (30 mL).
A solution of di-tert-butyl dicarbonate (11.9 g, 54.6 mmol, 1.01 equiv.) and TEA (24.6 g, 33.7 mL, 243 mmol, 4.5 equiv.) in dichloromethane (25 mL) was also metered in.
After completion of the addition the mixture was heated for 16 h under reflux.
After the reaction mixture had cooled it was filtered, the filtrate was washed with water (50 mL), dried over magnesium sulphate and freed from solvent under reduced pressure. N-boc-aminoacetonitrile (5.58 g, 66percent yield) remained as a brownish oil, which was used without further purification.
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 10, p. 1845 - 1895
[2] Synthetic Communications, 1994, vol. 24, # 12, p. 1767 - 1772
[3] Tetrahedron, 1988, vol. 44, # 18, p. 5833 - 5844
[4] Helvetica Chimica Acta, 1986, vol. 69, p. 1224 - 1262
[5] Patent: WO2017/81615, 2017, A1, . Location in patent: Page/Page column 33
[6] Acta Crystallographica Section C: Crystal Structure Communications, 1997, vol. 53, # 7, p. 959 - 961
[7] Patent: US2012/46301, 2012, A1, . Location in patent: Page/Page column 37
[8] Journal of Organic Chemistry, 1995, vol. 60, # 13, p. 4305 - 4308
[9] Patent: US5629152, 1997, A,
  • 3
  • [ 35150-09-5 ]
  • [ 85363-04-8 ]
Reference: [1] Synthetic Communications, 2009, vol. 39, # 3, p. 395 - 406
[2] Synthesis, 1988, # 3, p. 259 - 261
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4328 - 4332
[4] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 18, p. 5392 - 5396
  • 4
  • [ 4530-20-5 ]
  • [ 172876-96-9 ]
  • [ 85363-04-8 ]
Reference: [1] Chemical Science, 2017, vol. 8, # 3, p. 1790 - 1800
[2] Chimia, 2017, vol. 71, # 4, p. 226 - 230
  • 5
  • [ 51779-32-9 ]
  • [ 85363-04-8 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9152 - 9156
  • 6
  • [ 4530-20-5 ]
  • [ 85363-04-8 ]
Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
  • 7
  • [ 85363-04-8 ]
  • [ 96929-05-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 16, p. 3475 - 3485
[2] Tetrahedron, 1988, vol. 44, # 18, p. 5833 - 5844
  • 8
  • [ 67-56-1 ]
  • [ 868-59-7 ]
  • [ 85363-04-8 ]
  • [ 297165-32-3 ]
  • [ 96929-05-4 ]
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 2, p. 190 - 199
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