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[ CAS No. 55750-62-4 ] {[proInfo.proName]}

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Chemical Structure| 55750-62-4
Chemical Structure| 55750-62-4
Structure of 55750-62-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 55750-62-4 ]

CAS No. :55750-62-4 MDL No. :MFCD00043141
Formula : C11H10N2O6 Boiling Point : -
Linear Structure Formula :- InChI Key :JKHVDAUOODACDU-UHFFFAOYSA-N
M.W : 266.21 Pubchem ID :4620597
Synonyms :
BMPS

Calculated chemistry of [ 55750-62-4 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.36
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.0
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) : -9.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : -1.58
Log Po/w (WLOGP) : -1.85
Log Po/w (MLOGP) : -0.51
Log Po/w (SILICOS-IT) : -0.46
Consensus Log Po/w : -0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.17
Solubility : 182.0 mg/ml ; 0.684 mol/l
Class : Very soluble
Log S (Ali) : -0.03
Solubility : 246.0 mg/ml ; 0.925 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.36
Solubility : 116.0 mg/ml ; 0.438 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.85

Safety of [ 55750-62-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55750-62-4 ]

* 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 [ 55750-62-4 ]
  • Downstream synthetic route of [ 55750-62-4 ]

[ 55750-62-4 ] Synthesis Path-Upstream   1~11

  • 1
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YieldReaction ConditionsOperation in experiment
80%
Stage #1: at 70℃; Inert atmosphere
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 70℃;
EXAMPLE 1N-Maleimidopropionic acid NHS ester[0083] Maleic anhydride, β-alanine (1 mol eq.), and acetonitrile (ACN, 25 volumes) were charged to a vessel. The slurry was stirred under nitrogen and heated to 70 0C. The temperature was maintained at 70 0C for a further 5 to 8 hours. After cooling to 5 0C, NHS (1 mol eq.) was charged, followed by Λ/-(3-dimethylaminopropyl)-Λf'-ethylcarbodiimide hydrochloride (EDCI, 1 mol eq.). The temperature was maintained at 0 - 5 0C for 1 hour before adding a further charge of EDCI (1 mol eq.). The mixture was heated to 70 0C and maintained at this temperature for 7 hours. The reaction mixture was cooled to 200C and concentrated under vacuum at a maximum temperature of 45°C until the rate of solvent distillation was negligible. Dichloromethane (DCM, 40 volumes) was added to the residue, which was stirred until a solution was formed. This solution was washed with aqueous ammonium chloride (12 percent w/w, 25 wt eq.) then with aqueous sodium chloride (24 percent w/w, 25 wt eq.). The organic solution was dried by stirring with magnesium sulphate (1 wt eq.) at ambient temperature for 1 to 2 hours. The inorganics were filtered off under vacuum and the filter cake was washed with DCM (4 volumes). The filtrates were concentrated under vacuum, whilst gradually replacing DCM with isopropylacetate (IPAC). The residual slurry was cooled and stirred at ambient temperature for 1 hour before filtering under vacuum. The product filter cake was washed with IPAC (4 volumes) and then dried to constant mass under vacuum with slow rotation at 40 0C to yield the desired compound as an off white solid. The typical yield is 60 to 80 percent of the maximum theoretical yield.[0084] The product was characerised by NMR as follows: 1H NMR (400MHz, d6-DMSO): δ 2.80 (4H, br s), δ 3.05 (2H, t, J ~ 7Hz), δ 3.75 (2H, t J ~ 7Hz), δ 7.05 (2H, s).
60%
Stage #1: at 20℃; for 2.5 h;
Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃;
To a solution of maleic anhydride (2.00 g, 20.4 mmol) in 24 mL of DMF was added β-alanine (1.82 g, 20.4 mmol)and the mixture was stirred for 2.5 h at room temperature in which the solid was gradually dissolved to afford clear solution. The reaction was cooled in an ice bath and N-hydroxysuccinimide (HOSu) (2.88 g, 25 mmol) andN,N'-dicyclohexylcarbodiimide (8.24 g. 40.0 mmol) were successively added to the solution. After 30 min, the reaction was warmed to room temperature and stirred for 14 h. The reaction mixture was filtered through a cottonplug and the residue was washed with DCM and water. The filtrates were gathered and the organic layer was washed with satd NaHCO3 (three times) and brine, dried over Na2SO4 and concentrated to afford 1 (3.20 g, 60percent) as a white solid. 1H NMR (400 MHz, d6-DMSO): 2.78 (s, 4H), 3.03 (t, J = 6.9 Hz, 2H), 3.73 (t, J = 6.9 Hz, 2H),7.02 (s, 2H); 13C NMR (100 MHz, d6-DMSO): 25.4, 29.0, 32.7, 134.6, 166.7, 169.9, 170.5.
25% With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; On a solution of N-hydroxysuccinimide (12.6 mmol) and dicyclohexylcarbodiimide (20.3 mmol) at 0° C., corresponding acid (6 mmol) was added and allowed to react for 4 hours at room temperature. In the case of compound VIa, a solution of maleic anhydride (10 mmol) and β-alanine was added in N,N-dimethylformamide, which has been previously made react for 1 hour. After 4 hours, mixture was evaporated at reduced pressure and the crude was dissolved in dichloromethane and washed with water. Organic extracts were dried with anhydrous magnesium sulfate, filtered and evaporated to dryness. Resulting residue was recrystallized to give desired compound. [0112] Using this methodology, and corresponding acid, the following compounds were prepared: [0113] 3-succinimidyl maleimidopropionate (VIa, 25percent yield). 1H NMR (CDCl3) δ ppm: 2.82 (4H, s), 3.02 (2H, t, J=7.07 Hz), 3.94 (2H, t, J=7.07 Hz), 6.74 (2H, s); 13C NMR (CDCl3) δ ppm: 25.5 (2C, s), 29.7 (1C, s), 32.9 (1C, s), 134.3 (2C, s), 166.0 (1C, s), 168.7 (2C, s), 170.1 (2C, s).
Reference: [1] Patent: WO2011/23680, 2011, A2, . Location in patent: Page/Page column 13-14
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10198 - 10201[3] Angew. Chem., 2015, vol. 127, p. 10336 - 10339
[4] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10582 - 10585
[5] Journal of the American Chemical Society, 2004, vol. 126, # 3, p. 734 - 735
[6] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1721 - 1728
[7] Macromolecular Bioscience, 2012, vol. 12, # 9, p. 1209 - 1219
[8] Patent: US2013/273581, 2013, A1, . Location in patent: Paragraph 0111-0113
[9] Synthesis, 1991, # 10, p. 819 - 821
[10] Patent: WO2011/9047, 2011, A2, . Location in patent: Page/Page column 13
[11] Patent: US2013/157375, 2013, A1, . Location in patent: Paragraph 0103; 0104
[12] Chemical Communications, 2014, vol. 50, # 26, p. 3473 - 3475
[13] Patent: WO2014/100762, 2014, A1, . Location in patent: Paragraph 248
[14] Chemical Communications, 2015, vol. 51, # 53, p. 10758 - 10761
[15] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2356 - 2360[16] Angew. Chem., 2017, vol. 129, # 9, p. 2396 - 2400,5
  • 2
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Reference: [1] Analytical Chemistry, 2016, vol. 88, # 22, p. 10837 - 10841
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12243 - 12247[3] Angew. Chem., 2016, vol. 128, # 40, p. 12431 - 12435,5
[4] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[5] Tetrahedron Letters, 1998, vol. 39, # 11, p. 1321 - 1324
[6] Organic Letters, 2004, vol. 6, # 20, p. 3561 - 3564
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6400 - 6407
[8] Chemical Communications, 2011, vol. 47, # 25, p. 7068 - 7070
[9] Chemistry - A European Journal, 2011, vol. 17, # 46, p. 13059 - 13067
[10] Patent: US2014/56810, 2014, A1, . Location in patent: Paragraph 0181
[11] Organic and Biomolecular Chemistry, 2014, vol. 12, # 34, p. 6624 - 6633
[12] Journal of Controlled Release, 2015, vol. 220, p. 660 - 670
[13] Patent: WO2015/196167, 2015, A1, . Location in patent: Paragraph 0269; 0277
  • 3
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YieldReaction ConditionsOperation in experiment
64%
Stage #1: at 60℃; for 3 h;
Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 22℃; for 18.5 h;
To a solution of maleic anhydride (8; 86.0 g, 877 mmol) in DMF(1.03 L) was added β-alanine (9; 78.14 g, 877 mmol). The resultingsuspension was heated to 60 °C and, after 1 h, a solution was obtained.After 2 h, the mixture was cooled to 0–5 °C and N-hydroxysuccinimide(29; 126.17 g, 1.09 mol) was added followed by DCC(361.9 g, 1.75 mol) over 30 min in several portions while the internaltemperature was held below 22 °C. The thick, white slurry wasthen stirred at 20 °C for 18 h. The slurry was filtered and the solid(dicyclohexyl urea) was washed with H2O (1 L) and CH2Cl2 (1 L)and discarded. To the filtrates was added CH2Cl2 (1 L) and the phaseswere separated. The aqueous layer was extracted with CH2Cl2(2 × 300 mL) and the combined organic extracts were washed withH2O [500 mL; a small amount of brine (50 mL) was added to facilitatephase separation], sat. aq NaHCO3 (2 × 300 mL), and dried(MgSO4). The solvent was removed to give an oily, light tan solidthat was slurried in EtOH (520 mL) for 2 h at 20 °C. The solid wasfiltered, washed with EtOH (2 × 75 mL) and dried under vacuum at30 °C for 72 h to give 186.35 g (64percent) of NHS ester 30 as a whitesolid;32 HPLC purity: 96.6percent (areapercent); mp 169–171 °C.IR (ATR cell): 3088, 2954, 1825, 1783, 1705, 1583, 1446, 1433,1382, 1325, 1298, 1250, 1211, 1149, 1070, 1049, 998, 956, 901,836, 813, 786, 767, 756, 696, 651, 634, 596, 561, 544, 528 cm–1.1H NMR (400 MHz, DMSO-d6): δ = 2.80 (s, 4 H), 3.05 (t, J = 6.90Hz, 2 H), 3.75 (t, J = 6.78 Hz, 2 H), 7.05 (s, 2 H).13C NMR (100 MHz, DMSO-d6): δ = 25.38, 29.00, 32.67, 134.63,166.72, 169.93, 170.52.HRMS (ESI): m/z [M + H]+ calcd for C11H11N2O6: 267.06116;found: 267.06147.
Reference: [1] Synthesis (Germany), 2014, vol. 46, # 10, p. 1399 - 1406
  • 4
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Reference: [1] Patent: US9242011, 2016, B2, . Location in patent: Page/Page column 48
[2] Patent: US9480753, 2016, B2, . Location in patent: Page/Page column 120
  • 5
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YieldReaction ConditionsOperation in experiment
1.2 g With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2.5 h; 10152] 3-Maleimidopropionic acid (1.0 g, 5.9 mmol) was dissolved in tetrahydroffiran (20 ml). 2-Succinimido- 1,1,3,3- tetramethyluronium tetrafluoroborate (TSTU, 2.14 g, 7.1 mmol) and ethyldiisopropylamine (1.24 ml, 7.1 mmol) were added subsequently. N,N-Dimethylformamide (5 ml) was added. The reaction mixture was stirred at room temperature, while it was turning sluggish. The mixture was stirred for 2 mi N,N-Dimethylformamide (5 ml) was added. The mixture was stirred for 2.5 h at room temperature. It was diluted with dichloromethane (150 ml) and was washed subsequently with a 10percent aqueous solution of sodium hydrogensulphate (150 ml), a saturated aqueous solution of sodium hydrogencarbonate (150 ml) and water (150 ml). It was dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was recrystallized from ethyl acetate to give 1.20 g of 3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)propionic acid2,5-dioxopyrrolidiny-1 -yl ester. MS: mlz=289, required for [M+Na]: 28910154] ‘H-NMR (CDC13) ö 2.82 (m, 4H); 3.02 (t, 2H); 3.94 (t, 2H), 6.73 (s, 2H).
Reference: [1] Patent: US2015/376262, 2015, A1, . Location in patent: Paragraph 0150 - 0154
  • 6
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  • [ 68-12-2 ]
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Reference: [1] Patent: US2012/93840, 2012, A1,
  • 7
  • [ 5672-89-9 ]
  • [ 57079-11-5 ]
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Reference: [1] Synthetic Communications, 2008, vol. 38, # 2, p. 303 - 308
  • 8
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Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6400 - 6407
  • 9
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  • [ 538-75-0 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 17, p. 3400 - 3406
  • 10
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 5, p. 789 - 798
  • 11
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 20, p. 5032 - 5038
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