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[ CAS No. 55750-63-5 ] {[proInfo.proName]}

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Chemical Structure| 55750-63-5
Chemical Structure| 55750-63-5
Structure of 55750-63-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 55750-63-5 ]

CAS No. :55750-63-5 MDL No. :MFCD00043043
Formula : C14H16N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :VLARLSIGSPVYHX-UHFFFAOYSA-N
M.W : 308.29 Pubchem ID :5091655
Synonyms :
EMCS

Calculated chemistry of [ 55750-63-5 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 80.42
TPSA : 101.06 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : -0.51
Log Po/w (WLOGP) : -0.68
Log Po/w (MLOGP) : 0.31
Log Po/w (SILICOS-IT) : 0.67
Consensus Log Po/w : 0.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.9
Solubility : 38.6 mg/ml ; 0.125 mol/l
Class : Very soluble
Log S (Ali) : -1.14
Solubility : 22.1 mg/ml ; 0.0717 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.56
Solubility : 8.55 mg/ml ; 0.0277 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.01

Safety of [ 55750-63-5 ]

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 [ 55750-63-5 ]

* 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 [ 55750-63-5 ]
  • Downstream synthetic route of [ 55750-63-5 ]

[ 55750-63-5 ] Synthesis Path-Upstream   1~11

  • 1
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  • [ 55750-53-3 ]
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YieldReaction ConditionsOperation in experiment
95% With dicyclohexyl-carbodiimide In acetonitrile at 0 - 20℃; Inert atmosphere Under nitrogen protection, 4.7 g (22 mmol) of MC and 25 g (22 mmol) of HOSu were added to 50 ml of acetonitrile.Another 4.5 g (22 mmol) of DCC was dissolved in 25 ml of acetonitrile,Keeping the internal temperature around 0°C,It was slowly dropped into the reaction solution.The reaction solution was reacted at 0°C for 2 hours and then reacted overnight at room temperature.filter,The filter cake was washed with acetonitrile 10ml×3.The filtrate was concentrated to dryness under reduced pressure.The resulting oil was dried under reduced pressure at room temperature for 6 h to give 6.4 g of light brown solid.Yield 95percent.
70% With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3 h; Dicyclohexyl-carbodiimide (2.68 g, 13.02 mmol) and N-hydroxysuccinimide (1 .36 g, 1 1 .84 mmol) are added at room temperature to a stirrer solution of compound [4] (2.5 g, 1 1 .84 mmol) in anhydrous dichloromethane (15 mL) and the mixture stirred at room temperature for 3 hours. The white solid is filtered with dichloromethane to remove the dicyclohexylurea, the organic phase is washed with HCI 0.1 N and water, then dried over anhydrous sodium sulfate and the solvent removed by rotatory evaporation. The resulting residue is subjected to flash column chromatography with a medium pressure system Sepacore® Buchi (silica gel; gradient A: petroleum ether/B: ethyl acetate; Bpercent 0-80 in 15 minutes) to give the activated acid [5] as a white solid, 2.4 g (70percent). MS: m/z 309 [M+H]+.1H NMR (400 MHz, MeOD) δ 6.78 (s, 2H), 3.49 - 3.46 (m, 2H), 2.82 (s, 4H), 2.62 - 2.59 (m, 2H), 1 .78 - 1 .65 (m, 2H), 1 .64 - 1 .50 (m, 2H), 1 .46 - 1 .26 (m, 2H).13C NMR (100 MHz, MeOD) δ 169.8, 169.0, 167.3, 132.5, 35.4, 28.6, 26.1 , 23.8, 23.6, 22.3.
48% With dicyclohexyl-carbodiimide In ethyl acetate at 0 - 20℃; for 20 h; To a stirred solution of 6-(2,5-dioxo-2,5-dihydro-lH-pyrrol-l-yl)hexanoate (3.08 g, 14.6 mmol, 1.0 eq) and N-hydroxysuccinimide (1.76 g, 15.3 mmol, 1.05 eq) in EtOAc (30 mL) at 0 °C, was added dicyclohexylcarbodiimide (3.16 g, 15.3 mmol, 1.05 eq). The reaction was then allowed to warm to rt. After 20 h, the reaction was filtered and washed with EtOAc and the filtrate concentrated. The residue was purified by flash chromatography to yield the title compound (2.16 g, 48percent) as a clear oil that solidified slowly to a waxy white solid. NMR (400 MHz, Chloroform-i/) δ 6.71 (s, 2H), 3.56 (t, J = 7.2 Hz, 2H), 2.86 (s, 4H), 2.63 (t, J = 7.4 Hz, 2H), 1.80 (p, J= 7.4 Hz, 2H), 1.73 - 1.57 (m, 2H), 1.50 - 1.35 (m, 2H). m/z calcd. for C14H16N206 = 308.10. Found [M+H]+ = 309.13. Rf = 0.28 (50percent EtOAc/Hex).
48% With dicyclohexyl-carbodiimide In ethyl acetate at 0 - 20℃; for 20 h; To a stirred solution of 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-l-yl)hexanoate (3.08 g, 14.6 mmol, 1.0 eq) and N-hydroxysuccinimide (1.76 g, 15.3 mmol, 1.05 eq) in EtOAc (30 mL) at 0 °C,was added dicyclohexylcarbodiimide (3.16 g, 15.3 mmol, 1.05 eq). The reaction was then allowed towarm to rt. After 20 h, the reaction was filtered and washed with EtOAc and the filtrate concentrated. The residue was purified by flash chromatography to yield the title compound (2.16 g, 48percent) as a clear oil that solidified slowly to a waxy white solid. ‘H NMR (400 MHz, Chloroform-d) ö 6.71 (s, 2H), 3.56 (t, J = 7.2 Hz, 2H), 2.86 (s, 4H), 2.63 (t, J = 7.4 Hz, 2H), 1.80 (p, J = 7.4 Hz, 2H), 1.73 — 1.57 (m,2H), 1.50 1.35 (m, 2H). m/z calcd. for C,4H,6N206 = 308.10. Found [M+H] = 309.13. Rf= 0.28 (50percent EtOAc/Hex)

Reference: [1] Patent: CN107789630, 2018, A, . Location in patent: Paragraph 0064; 0065; 0066
[2] Patent: WO2018/178060, 2018, A1, . Location in patent: Page/Page column 58; 60; 61
[3] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[4] Patent: WO2015/95953, 2015, A1, . Location in patent: Page/Page column 118
[5] Patent: WO2016/41082, 2016, A1, . Location in patent: Page/Page column 97; 98
[6] Organic and Biomolecular Chemistry, 2014, vol. 12, # 34, p. 6624 - 6633
[7] Patent: CN108743968, 2018, A, . Location in patent: Paragraph 0007; 0008; 0009
  • 2
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  • [ 55750-53-3 ]
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YieldReaction ConditionsOperation in experiment
70% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 1 h; Inert atmosphere 6-Maleimidohexanoic acid N-hydroxysuccinimide ester 4. Sodium bicarbonate (0.0512 g, 0.483 mmol ) was added to a solution of 6-maleimidocaproic acid (0.211 g, 1.000 mmol) in DI water (10 mL). After the reagents were dissolved in DI water, the DI water was evaporated by blowing with air. The resulting solid was dissolved in anhydrous DMF (3 mL) and the solution was cooled to 0 °C. Disuccinimide carbonate (0.282 g, 1.10 mmol) was added into the solution and the reaction was stirred at 0 °C for 1 h. CH2C12 (25 mL) was added into reaction which was then washed with water (3 x 10 mL). The resulting organic layer was dried over Na2S04, concentrated under reduced pressure, and purified by flash chromatography using a pre-packed 25 g silica column [solvent A: MeOH; solvent B: CH2C12; gradient: 0percentA / 100percentB (1 CV), 0percentA / 100percentB→ 2percentA / 98percentB (10 CV), 2percentA / 98percentB (2 CV); flow rate: 25 mL/min; monitored at 210 and 280 nm] to afford ester 4 (0.215 g, 0.697 mmol, 70percent yield) as a light yellow liquid. [000194] NMR (500 MHz, CDC13) 66.69 (2H, s), 3.53 (2H, t, J= 7.1 Hz), 2.83 (4H, s), 2.60 (2H, t, .7=7.4 Hz), 1.78 (2H,p, .7=7.5 Hz), 1.63 (2H,p, .7=7.4 Hz), 1.41 (2H,p,J=7.6 Hz). [000195] 13CNMR(125 MHz, CDC13) δ 170.9, 169.2, 168.5, 134.2,37.5,30.8,28.1,25.9,25.7,24.1.
Reference: [1] Journal of the American Chemical Society, 1994, vol. 116, # 14, p. 6101 - 6106
[2] Patent: WO2017/66668, 2017, A1, . Location in patent: Paragraph 000193-000195
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 41, p. 13091 - 13096
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4516 - 4520
[3] Synthesis (Germany), 2014, vol. 46, # 22, p. 3085 - 3096
  • 4
  • [ 74124-79-1 ]
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Reference: [1] Biochemical Pharmacology, 2007, vol. 73, # 5, p. 620 - 631
[2] Patent: WO2007/90094, 2007, A2, . Location in patent: Page/Page column 35; 4/9
  • 5
  • [ 60-32-2 ]
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Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174
[2] Patent: WO2015/95953, 2015, A1,
[3] Patent: WO2016/41082, 2016, A1,
[4] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[5] Patent: CN107789630, 2018, A,
[6] Patent: WO2018/178060, 2018, A1,
[7] Patent: CN108743968, 2018, A,
  • 6
  • [ 6066-82-6 ]
  • [ 57079-14-8 ]
  • [ 55750-63-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 5, p. 789 - 798
[2] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174
  • 7
  • [ 6066-82-6 ]
  • [ 55750-53-3 ]
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  • [ 57-13-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406
  • 8
  • [ 6066-82-6 ]
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  • [ 55750-63-5 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174
  • 9
  • [ 660-88-8 ]
  • [ 55750-63-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 34, p. 6624 - 6633
  • 10
  • [ 60-32-2 ]
  • [ 55750-63-5 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9169 - 9174
  • 11
  • [ 55750-63-5 ]
  • [ 159857-81-5 ]
Reference: [1] Patent: WO2017/66668, 2017, A1,
[2] Patent: WO2017/66668, 2017, A1,
[3] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[4] Patent: CN107789630, 2018, A,
[5] Patent: CN108743968, 2018, A,
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