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N-Succinimidyl Methacrylate
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[ CAS No. 38862-25-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 38862-25-8
Chemical Structure| 38862-25-8
Chemical Structure| 38862-25-8
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Quality Control of [ 38862-25-8 ]

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Product Details of [ 38862-25-8 ]

CAS No. :38862-25-8 MDL No. :MFCD15072193
Formula : C8H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ACGJEMXWUYWELU-UHFFFAOYSA-N
M.W : 183.16 Pubchem ID :10130244
Synonyms :

Calculated chemistry of [ 38862-25-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.38
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.48
TPSA : 63.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 0.19
Log Po/w (WLOGP) : -0.21
Log Po/w (MLOGP) : 0.34
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.9
Solubility : 23.2 mg/ml ; 0.127 mol/l
Class : Very soluble
Log S (Ali) : -1.09
Solubility : 15.0 mg/ml ; 0.0821 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.63
Solubility : 43.3 mg/ml ; 0.237 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.31

Safety of [ 38862-25-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38862-25-8 ]

* 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.

  • Downstream synthetic route of [ 38862-25-8 ]

[ 38862-25-8 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 6066-82-6 ]
  • [ 920-46-7 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine In dichloromethane at 20℃; for 24h; Cooling with ice;
68% With triethylamine In tetrahydrofuran at 0 - 20℃;
67% With triethylamine In dichloromethane at 20℃; Cooling with ice; Inert atmosphere;
62% With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;
With triethylamine In chloroform 1 Step D1: Step D1: Synthesis of N-methacryloyloxysuccinimide (NMAS): Methacryloyl chloride (10mL, 89mmol) was added dropwise to a stirred solution of N-hydroxysuccinimide (11g, 98mmol) and triethylamine (13mL, 98mmol) in chloroform at 0°C. After stirring for 4 h at 0°C, the reaction mixture was washed with ice-cold saturated sodium bicarbonate solution four times and dried on MgSO4 overnight. Then, the solution was filtered and chloroform was removed by evaporation. Yield ca. 75%. RMN 1H (400MHz, DMSO-d6) δ (ppm/TMS) : 1.95 (s, 3H, CH2=C(CH3), 2.80 (s, 4H, - (C=O)-CH2-CH2-(C=O)-), 5.68 ; 6.28 (d, CH2=C(CH3))
With triethylamine In dichloromethane at 5℃; for 1h; A2 To N-hydroxysuccinimide (6.6 g, 57 mmol) in dichloromethane (12 ml) was added dropwise a dichloromethane (12 ml) solution of methacryloyl chloride (6.0 g, 57 mmol) simultaneously with a dichloromethane solution (12 ml) of triethylamine (5.8 g, 57 mmol) maintaining the temperature below 5 °C. After complete addition the reaction mixture was further stirred for 1 h and then washed with aqueous sodium hydrogen carbonate (0.1 M) and water (3 times). The organic phase was then isolated and dried with magnesium sulfate. The solvent was removed to leave the product as a white solid which was recrystalised from ethyl acetate: hexane. Mass 8 g, m. p. = 102°C. (1H, 500MHz, DMSO-d6) : 2.00 (3H, s, CH3), 2. 84 (4H, s, (CH2) 2), 6.09 (1H, s, =CH2), 6.34 (1H, s, =CH2).

Reference： [1]Cao, Hongliang; Dong, Yixiao; Bre, Ligia; Tapeinos, Christos; Wang, Wenxin; Pandit, Abhay [RSC Advances, 2016, vol. 6, # 12, p. 9604 - 9611]
[2]Shunmugam, Raja; Gabriel, Gregory J.; Smith, Cartney E.; Aamer, Khaled A.; Tew, Gregory N. [Chemistry - A European Journal, 2008, vol. 14, # 13, p. 3904 - 3907]
[3]Dan, Krishna; Bose, Nivedita; Ghosh, Suhrit [Chemical Communications, 2011, vol. 47, # 46, p. 12491 - 12493]
[4]Tarasow, Theodore M.; Tarasow, Sandra L.; Tu, Chi; Kellogg, Elizabeth; Eaton, Bruce E. [Journal of the American Chemical Society, 1999, vol. 121, # 15, p. 3614 - 3617]
[5]Current Patent Assignee: BIOWINTECH; COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - EP2813249, 2014, A1 Location in patent: Page/Page column
[6]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 55-56
  • 2
  • [ 38862-25-8 ]
  • [ 107-15-3 ]
  • [ 63298-57-7 ]
YieldReaction ConditionsOperation in experiment
161 mg In tetrahydrofuran at 0 - 20℃;
Reference： [1]Tarasow, Theodore M.; Tarasow, Sandra L.; Tu, Chi; Kellogg, Elizabeth; Eaton, Bruce E. [Journal of the American Chemical Society, 1999, vol. 121, # 15, p. 3614 - 3617]
  • 3
  • [ 38862-25-8 ]
  • [ 189324-13-8 ]
  • N-metacryloxysuccinimide; 2-bromo-2-methyl-(2-hydroxyethyl)prppanoate; copolymer of [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With [2,2]bipyridinyl; copper(I) bromide In dimethyl sulfoxide at 100℃;
Reference： [1]Godwin, Antony; Hartenstein, Markus; Mueller, Axel H. E.; Brocchini, Stephen [Angewandte Chemie - International Edition, 2001, vol. 40, # 3, p. 594 - 597]
  • 4
  • [ 38862-25-8 ]
  • [ 79-06-1 ]
  • Polymer, radical-initiated solution copolymerization, Mn = 70000, Mw/Mn = 2.00; Monomer(s): acrylamide; methacryloyloxysuccinimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With azobisisobutyronitrile In N,N-dimethyl-formamide at 60℃; for 1.5h;
Reference： [1]Kondo, Shin-Ichi; Shichijyou, Daisuke; Sasai, Yasushi; Yamauchi, Yukinori; Kuzuya, Masayuki [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 7, p. 863 - 865]
  • 5
  • [ 38862-25-8 ]
  • [ 79-06-1 ]
  • Polymer, radical-initiated solution copolymerization, Mn = 32000, Mw/Mn = 1.63; Monomer(s): acrylamide; methacryloyloxysuccinimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With azobisisobutyronitrile In N,N-dimethyl-formamide at 60℃; for 1.5h;
Reference： [1]Kondo, Shin-Ichi; Shichijyou, Daisuke; Sasai, Yasushi; Yamauchi, Yukinori; Kuzuya, Masayuki [Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 7, p. 863 - 865]
  • 6
  • [ 600-00-0 ]
  • [ 38862-25-8 ]
  • [ 80-62-6 ]
  • polymer, Mn 11300, MWD 1.23; monomer(s): methacrylic acid N-hydroxysuccinimide ester; methyl methacrylate; ethyl 2-bromoisobutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide In methoxybenzene at 90℃; for 0.17h;
Reference： [1]Shunmugam, Raja; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13567 - 13572]
  • 7
  • [ 600-00-0 ]
  • [ 38862-25-8 ]
  • [ 80-62-6 ]
  • polymer, Mn 10000, MWD 1.23; monomer(s): methacrylic acid N-hydroxysuccinimide ester; methyl methacrylate; ethyl 2-bromoisobutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide In methoxybenzene at 90℃; for 2h;
Reference： [1]Shunmugam, Raja; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13567 - 13572]
  • 8
  • [ 600-00-0 ]
  • [ 38862-25-8 ]
  • [ 97-88-1 ]
  • polymer, Mn 9700, MWD 1.12; monomer(s): methacrylic acid N-hydroxysuccinimide ester; n-butyl methacrylate; ethyl 2-bromoisobutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper(I) bromide In methoxybenzene at 90℃; for 2h;
Reference： [1]Shunmugam, Raja; Tew, Gregory N. [Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13567 - 13572]
  • 9
  • [ 6066-82-6 ]
  • [ 35660-94-7 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In dichloromethane at 20℃; for 3h;
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 10
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 3.6E4 g/mol, intrinsic viscosity = 17.0 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 11
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 3.9E4 g/mol, intrinsic viscosity = 20.3 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 12
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 4.0E4 g/mol, intrinsic viscosity = 19.0 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 13
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 5.3E4 g/mol, intrinsic viscosity = 25.0 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 14
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 5.8E4 g/mol, intrinsic viscosity = 20.6 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 15
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 1.1E4 g/mol, intrinsic viscosity = 27.5 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 16
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 13E4 g/mol, intrinsic viscosity = 18 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 17
  • [ 38862-25-8 ]
  • [ 141-32-2 ]
  • polymer, Mw = 22E4 g/mol, free radical copolymerization; monomer(s): N-methacryloxysuccinimide; butyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 18
  • [ 38862-25-8 ]
  • polymer, Mw = 0.6E4 g/mol, intrinsic viscosity = 6.24 cm3/g, free radical copolymerization; monomer(s): N-methacryloxysuccinimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide
Reference： [1]Alb, Alina M.; Enohnyaket, Pascal; Drenski, Michael F.; Shunmugam, Raja; Tew, Gregory N.; Reed, Wayne F. [Macromolecules, 2006, vol. 39, # 24, p. 8283 - 8292]
  • 19
  • [ 6066-82-6 ]
  • dicyclohexylcarbodiimide (DCC) [ No CAS ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
With urea In N,N-dimethylformamide (DMF); dichloromethane; N,N-dimethyl-formamide 1.2 1.2 1.2 Preparation of N-hydroxysuccinimide ester 2 Compound 1 (1 g, 1.7 mmol) was dissolved in N,N-dimethylformamide (DMF) (10 mL) in a 25 mL round-bottom flask. 1-Hydroxysuccinimide (0.3 g, 2.6 mmol) and dicyclohexylcarbodiimide (DCC) (0.55 g, 2.6 mmol) dissolved in DMF (3 mL) were added drop-wise with stirring. The mixture was maintained overnight and filtered to remove the urea. The urea was washed with DMF. The solvents were removed by rotary evaporation. The residue was dissolved in dichloromethane and washed with water 3 times. The organic layer was dried over MgSO4, filtered and the solvent removed. The residue was vacuum dried to a dark red solid. The product, 2, was used without further purification. Yield 0.94 g, 98%.
Reference： [1]Current Patent Assignee: HSBC HOLDINGS PLC - US2005/214833, 2005, A1
  • 20
  • 1-(2-methylpyrid-4-yl)piperazine dihydrochloride [ No CAS ]
  • [ 38862-25-8 ]
  • 1-[4-(6-bromonaphth-2-ylsulphonyl)benzoyl]-4-(2-methylpyrid-4-yl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane 41 EXAMPLE 41 EXAMPLE 41 A mixture of 1-(2-methylpyrid-4-yl)piperazine dihydrochloride (145 mg), triethylamine (0.16 ml), N-hydroxysuccinimide ester from part (iv) of Example 26 (244 mg) and DMF (10 ml) was stirred for 16 hours. The solvent was evaporated and the residue dissolved in methylene chloride and washed with water. The aqueous washings were extracted with further methylene chloride and the combined organic extracts dried (MgSO4) and evaporated. The residue was further purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluant and the resulting solid triturated under diethyl ether. There was thus obtained 1-[4-(6-bromonaphth-2-ylsulphonyl)-benzoyl]-4-(2-methylpyrid-4-yl)piperazine (115 mg); NMR Spectrum (DMSO-d6+D2O) 2.28 (s, 3H), 3.20-3.48 (m, 6H), 3.66 (bs, 2H), 6.61 (d, 1H), 6.67 (s, 1H), 7.63 (d, 2H), 7.80 (d, 1H), 7.97 (t, 2H), 8.06-8.17 (m, 4H), 8.32 (s, 1H), 8.72 (s, 1H); Mass Spectrum m/z 550/552 (M+H); Elemental Analysis Found C, 57.7; H 4.2; N, 7.7, S, 5.8; C27H24BrN3O3S 0.5H2O requires: C, 58.0; H, 4.5; N, 7.5, S, 5.7%.
Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US2003/207882, 2003, A1
  • 21
  • [ 6066-82-6 ]
  • 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) [ No CAS ]
  • 1-(4-aminosulfonylphenyl)-4-(4-chlorophenyl)pyrazole-3-acetic acid [ No CAS ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane 3.4 EXAMPLE 3 Step 4. Preparation of [[1-[4-(aminosulfonyl)phenyl]=5-(4-chlorophenyl)-1H-pyrazol-3-yl ]-N-hydroxy-N-methylacetamide To a stirred solution of the 1-(4-aminosulfonylphenyl)-4-(4-chlorophenyl)pyrazole-3-acetic acid from step 3 (0.240 g, 0.613 mmol) in dioxane (6mL) was added N-hydroxysuccinimide (0.085 g, 0.735 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.129 g, 0.674 mmol). After stirring overnight, the reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The ethyl acetate phase was washed with KHSO4, NaHCO3, and brine, dried over MgSO4, filtered and concentrated in vacuo yielding the crude N-hydroxysuccinimide ester.
Reference： [1]Current Patent Assignee: PFIZER INC - US2002/58810, 2002, A1
  • 22
  • [ 74124-79-1 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dimethyl sulfoxide; N,N-dimethyl-formamide 26 Preparation of Dye-NHS Ester Example 26 Preparation of Dye-NHS Ester The dye was dissolved in anhydrous DMF or DMSO at a concentration of 50mg/mL and 2 equivalents of Et3N followed by 2 equivalents of disuccinimidyl carbonate were added and the solution stirred at 50° C. for 16 hours under argon. The reaction was cooled and the N-hydroxysuccinimide ester precipitated with ethylacetate.
With pyridine In <i>N</i>-methyl-acetamide 3 Example 3 Example 3 Preparation of STR5 3.0 g (6.1 mmol) of the compound (1) of the formula STR6 are dissolved in 90 ml of dimethylformamide. The solution is heated to 50° C. 1.5 ml of pyridine (1.47 g, 18.5 mmol) and 5.7 g of disuccinimidyl carbonate (22.1 mmol) are added at this temperature. After stirring at 50°to 60° C. for 3 h, conversion to the N-hydroxysuccinimide ester is complete. After removing the dimethylformamide by distilling off in vacuo, the remaining residue is purified by column chromatography (silica gel, eluent toluene/ ethanol 1:2).
Reference： [1]Current Patent Assignee: ARSENAL CAPITAL PARTNERS LP - US6403807, 2002, B1
[2]Current Patent Assignee: SIEMENS AG - US5547860, 1996, A
  • 23
  • [ 4418-61-5 ]
  • [ 157014-13-6 ]
  • [ 38862-25-8 ]
  • 4-(7-Methyl-2,4-bis-pyrrolidin-1-yl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-(1H-tetrazol-5-yl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-(Dimethylamino)pyridine In <i>N</i>-methyl-acetamide; chloroform 187 4-(7-Methyl-2,4-bis-pyrrolidin-1-yl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-(1H-tetrazol-5-yl)-benzamide (VII) EXAMPLE 187 4-(7-Methyl-2,4-bis-pyrrolidin-1-yl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-(1H-tetrazol-5-yl)-benzamide (VII) A mixture of 247 mg of the N-hydroxysuccinimide ester from EXAMPLE 186 in 50 ml of dimethylformamide is treated with 110 mg of 5-aminotetrazole followed by 71 mg of dimethylaminopyridine. The mixture is stirred for 3 hrs and then heated at reflux for 1 hr. The dimethylformamide is removed at reduced pressure to give a solid which is dissolved in chloroform with the aid of a small amount of methanol. The resulting mixture is washed with saline. The aqueous layer is extracted with six portions of chloroform. The combined organics are dried and filtered. The solids are washed with dimethylformamide. The filtrate is concentrated to give an orange solid which is chromatographed over silica gel (elution with 15-20% methanol saturated with ammonia-dichloromethane) to give the title compound, mp >310°; NMR (DMSO) 8.15-8.12, 7.76-7.73, 7.24, 6.77, 3.89-3.60, 3.60-3.46, 2.07-1.80δ; MS calc'd for C23 H26 N10 O=459.2369, found=459.2374.
Reference： [1]Current Patent Assignee: PFIZER INC - US5502187, 1996, A
  • 24
  • [ 38862-25-8 ]
  • [ 107-35-7 ]
  • [ 157014-13-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In tetrahydrofuran; sodium hydroxide; water 186 2-[4-(7-Methyl-2,4-bis-pyrrolidin-1-yl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoylamino]ethanesulfonic acid ammonium salt (VII) A suspension of 249 mg of this intermediate N-hydroxysuccinimide ester in 50 ml of THF is warmed slightly until the solid goes into mixture and then treated with 662 mg of taurine in 5.2 ml of 1.0N aqueous sodium hydroxide followed by 5 ml of water. The mixture is stirred for 2 hrs and then concentrated under reduced pressure. The resulting residue is dissolved in water and treated with 5% aqueous hydrochloric acid. The pH of the mixture is adjusted to pH 4. The layers were separated and finally the aqueous layer is extracted with chloroform. The combined organics are dried and concentrated to give 621 mg of a solid which is chromatographed over silica gel (elution with 15-20% methanol saturated with ammonia-dichloromethane) to give the title compound, mp 185°-190°; NMR (DMSO) 8.63-8.51, 7.86-7.84, 7.68-7.65, 7.36, 7.19, 7.02, 6.74, 3.88-3.26, 2.79-2.64, 2.13-1.80δ; MS calc'd for C24 H30 N6 O4 S+H=499.2127, found: 499.2143.
Reference： [1]Current Patent Assignee: PFIZER INC - US5502187, 1996, A
  • 25
  • [ 38862-25-8 ]
  • [ 4070-48-8 ]
  • [ 2389-60-8 ]
  • [ 134507-52-1 ]
YieldReaction ConditionsOperation in experiment
81% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate 2.B B. B. Synthesis of N-α-carbobenzoxy-N-ε-tert-butoxycarbonyl-lysyl-valine, methyl ester To a solution of valine methyl ester (8.38 g, 50 mmol) and diisopropylethylamine (12.7 mL, 50 mmol) in 150 mL THF was added N-α-carbobenzoxy-N-ε-tert-butoxycarbonyl lysine, N-hydroxysuccinimide ester (23.9 g, 50 mmol), followed by an additional 50 mL THF. After 2 h the solvent was removed by evaporation and 50 mL ethyl acetate added to the residue. This solution was washed sequentially with 200 mL 5 % citric acid, 200 mL saturated sodium bicarbonate and 200 mL saturated brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The resulting oil was dissolved in minimal ethyl acetate, 200 mL ether and 200 mL hexanes. The title compound was isolated by filtration and dried to yield 20 g (40.5 mmol, 81% yield).
Reference： [1]Current Patent Assignee: IBA ION BEAM APPLICATIONS SA - US5783170, 1998, A
  • 26
  • [ 38862-25-8 ]
  • None [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methacrylic acid methyl ester With ethyl 2-bromoisobutyrate In dimethyl sulfoxide Stage #2: methacrylic acid N-hydroxysuccinimide ester In dimethyl sulfoxide A16; A17; A18 Examples A1-A22; These polymeric dispersants were prepared by atom transfer radical polymerisation according to the method of Haddleton et al. (Macromolecules, 1997, 30, 2190-2193). Discrete polymer segments were built up by sequential (co)monomer addition; the compositions of the (co)monomer batches used are given in Table 1 below.The initiator for atom transfer radical polymerisation was added as part of the first batch and is noted in Table 1. The initiator used was either ethyl-2-bromo-ωø-butyrate [E2BiB] (from Sigma- Aldricb), a poly(ethylene glycol) derived macro-initiator [PEG-Br] with a molecular weight of approximately 2000g/mole, prepared according to the method of Jankova et al. (Macromolecules, 1998, 31, 538-541) or a bis-phenol derived dibromide [BPDB] made according to the following procedure. Preparation of 4.4'-isopropylidene diphenyl bis-2-bromo-2-methylpropionate A slurry of 1 part of 4,4'-isopropylidene diphenol in 8.7 parts of toluene was deoxygenated by sparging with dry nitrogen gas for 1 hour. 1.06 parts of triethylamine were added to the slurry resulting in a clear solution. The reaction mixture was cooled to 0°C before 2.4 parts of 2-bromoisobutyryl bromide were added drop- wise over 90 minutes and then the reaction mixture left to stir for 24hours at 20°C. The resultant precipitate was removed by filtration and the remaining light brown solution reduced under vacuum to give a brown solid, which was recrystallised from methanol to yield the product as white flakes.After polymerization was completed the polymers were isolated by methods common in the art. In the cases of Al -Al 5, the solutions were passed through a column of activated basic alumina to remove copper salts and isolated by precipitation into petroleum ether (60-80°C). In the cases of Al 6-Al 8, the polymer solutions were treated with aqueous ammonium hydroxide (1.2 molar equivalents with respect to the NHSMA monomer) to deprotect the carboxylic acid groups and the polymer isolated by precipitation into acetone at -79°C. In the cases of A19-A22, the polymer solutions were passed through a column of activated basic alumina to remove copper salts and the solvent removed under vacuum. The polymer was subsequently dissolved into water at pH 10 (addition of NaOH) and stirred for 24 hours at 20°C to deprotect the carboxylic acid groups. EPO TABLE 1
Reference： [1]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2006/97690, 2006, A1 Location in patent: Page/Page column 12-13
  • 27
  • c(Trt) [ No CAS ]
  • aqueous KHSO4 [ No CAS ]
  • [ 38862-25-8 ]
  • [ 75-09-2 ]
  • (2-Triphenylmethylthioacetyl)-glycyl-(S-triphenylmethyl) cysteine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; sodium hydrogencarbonate In 1,2-dimethoxyethane; N,N-dimethyl-formamide 4.A A. A. (2-Triphenylmethylthioacetyl)-glycyl-(S-triphenylmethyl) cysteine (XVIII) A solution of compound (VIII) (4.88 g, 10 mmol) was dissolved in a mixture of DME (50 ml) and DMF (20 ml) and cooled to 0° C., and treated with a solution of S-(triphenylmethyl)cysteine (See Hiskey and Adams, J. Org. Chem. 3: 1340, (1965)) (3.63 g, 10 mmol) in DME (25 ml) and 1M aqueous NaOH (10 ml, 10 mmol) containing NaHCO3 (0.84 g, 10 mmol). The resulting solution was allowed to warm to room temperature after stirring for 50 minutes, 1M aqueous KHSO4 (30 ml) was added and a white gummy solid precipitated. The resulting mixture (pH 4) was extracted with CH2 Cl2 (3*50 ml). The CH2 Cl2 was washed with water, then saturated brine, dried (MgSO4), filtered and evaporated to give compound (XVIII) as an oil.
Reference： [1]Current Patent Assignee: CINCINNATI CHILDREN&apos;S HOSPITAL MEDICAL CENTER; UMASS MEMORIAL HEALTH CARE INC; HARVARD UNIVERSITY; MASSACHUSETTS INSTITUTE OF TECHNOLOGY - US4673562, 1987, A
  • 28
  • [ 6066-82-6 ]
  • N-(c-NOPY)-Gly [ No CAS ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran V N-Hydroxysuccinimide Ester of N-(1-Cyclohexyl-4-nitro-2-oxo-3-pyrrolin-3-yl)glycine (8a, c-NOPY-Gly-OSu) EXAMPLE V Preparation of an Active Ester of NOPYE Amino Acid N-Hydroxysuccinimide Ester of N-(1-Cyclohexyl-4-nitro-2-oxo-3-pyrrolin-3-yl)glycine (8a, c-NOPY-Gly-OSu) To a solution of 0.432 g (3.75 mmol) of N-hydroxysuccinimide (HOSu) and 0.71 g (2.5 mmol) of N-(c-NOPY)-Gly (7a) in 10 mL of tetrahydrofuran (THF) was added 0.6 g (2.9 mmol) of di-dyclohexylcarbodiimide (DDC), and the mixture was stirred overnight at room temperature. The crystalline precipitate that separated was removed by filtration and extracted with 20 mL of boiling THF to recover a quantity of the N-hydroxysuccinimide ester that separated in the precipitate along with N,N'-dicyclohexylurea (DCU). After cooling and filtering to remove DCU, the extract was combined with the first filtrate, and the solution was taken to dryness under reduced pressure in a rotary evaporator. The residue was treated with 5 mL of hot methylene chloride, and the resulting solution was diluted with 10 mL of petroleum ether (bp 30°-60° C.). A light tan crystalline precipitate separated; mp 180°-181° C. The yield was 0.723 g (76%). Recrystallization from methylene chloride-petroleum ether (bp 30°-60° C.) raised the melting point to 192°-194° C.; IR (Nujol) 3.04, 5.42, 5.60, 5.76, 5.92, 6.06, 6.96, 7.03, 7.15, 7.28, 7.81, 7.93, 8.05, 8.23, 8.40, 9.23 μm. Anal. Calcd for C16 H20 N4 O7: C, 50.52; H, 5.30; N, 14.73. Found: C, 50.42; H, 5.39; N, 14.58.
Reference： [1]Current Patent Assignee: Southwick; Philip L. - US4739076, 1988, A
  • 29
  • [ 6066-82-6 ]
  • [ 78261-89-9 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide 4.E E. E. N-HYDROXYSUCCINIMIDE ESTER OF 3-β-GALACTOSYLOXY-4-NITROBENZOIC ACID (VII) 3-β-Galactosyloxy-4-nitrobenzoic Acid (55.2 g, 0.160 mole), N-hydroxysuccinimide (20 g, 0.174 mole), and EDCI (35 g, 0.183 mole) were dissolved in DMF (200 ml). After two hours, the reaction was complete by TLC -(10-20% MeOH/CHCl3), and showed some minor impurities in addition to the desired compound VII. The solution was used without further treatment.
Reference： [1]Current Patent Assignee: SIEMENS AG - US4501692, 1985, A
  • 30
  • [ 38862-25-8 ]
  • [ 72155-45-4 ]
  • [ 66605-57-0 ]
YieldReaction ConditionsOperation in experiment
With lithium borohydride In tetrahydrofuran 4.a (a) (a) N-[(1,1-Dimethylethoxy)carbonyl]-L-phenylalaninal To a solution of lithium borohydride (940 mg. 43.2 mmole) in dry tetrahydrofuran (90 ml.) cooled in an ice-bath under nitrogen is added a solution containing N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine, N-hydroxysuccinimide ester (6.0 g., 16.6 mmole) [prepared according to the procedure of Anderson et al., JACS, Vol. 86, p.1839 (1964)]in tetrahydrofuran (60 ml.). The addition is carried out over a period of 5 minutes. After an additional 20 minutes at 0°, the reaction mixture is poured into 1l. of cold 10% potassium bisulfate. The mixture is extracted with ethyl acetate (4*150 ml) and the combined organic extracts are rinsed with saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, and concentrated in vacuo to give 3.8 g. of crude product. Flash chromatography (Merck 9385 silica gel, 250 g.) eluding with chloroform:methanol (100:1, 50:1, and finally 25:1) gives 2.4 g. of purified product. Recrystallization from etherhexane gives 1.9 g. of (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-2-phenylmethyl-1-ethanol; m.p. 95°-96°; [α]D=- 27.5° (c=1, methanol). TLC (silica gel; chloroform:methanol:acetic acid, 25:1:1) Rf =0.54. Anal. calc'd. for C14 H21 NO3 C, 66.90; H, 8.42; N, 5.57 Found: C, 67.02; H, 8.49; N, 5.23.
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4885292, 1989, A
  • 31
  • [ 645-65-8 ]
  • [ 70-34-8 ]
  • imidazole-N-(DNP)-4-acetic acid [ No CAS ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
91.A A. A. Activated imidazole-4-acetic acid Imidazole-4-acetic acid was reacted with 2,4-dinitrofluoro benzene. The resulting imidazole-N-(DNP)-4-acetic acid was converted to its N-hydroxy succinimide ester by treating with NHS/EDAC according to the procedure of Example 78.
Reference： [1]Current Patent Assignee: NIELSEN PETER EIGIL; DORTE BUCHARDT; IONIS PHARMACEUTICALS; BUCHARDT DORTE; PETER EIGIL NIELSEN; BUCHARDT DORTE LF - EP804456, 2002, B1
  • 32
  • [ 6066-82-6 ]
  • [ 113180-63-5 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane Preparation of Compound 6 STR27 Preparation of Compound 6 STR27 p-Trifluoroacetamidophenylacetyl chloride was treated with N-hydroxysuccinimide and triethylamine in dichloromethane to provide Compound 6 as a white solid after purification in the manner described above with reference to Compound 5.
Reference： [1]Current Patent Assignee: SCRIPPS HEALTH INC; SCRIPPS RESEARCH - US5030717, 1991, A
  • 33
  • (N-benzyloxycarbonyl)leucine [ No CAS ]
  • [ 38862-25-8 ]
  • [ 2673-19-0 ]
  • benzyloxycarbonyl-Leu-Asp-H [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With 4-methyl-morpholine; In dichloromethane; Part A [(N-Benzyloxycarbonyl)Leucinyl]Aspartic Acid, betatert-Butyl, alpha-Methyl Ester To a solution of (N-benzyloxycarbonyl)leucine, N-hydroxysuccinimide ester (4.54 g, 12.5 mmol) and aspartic acid, beta-tert-butyl, alpha-methyl ester hydrochloride (3.00 g, 12.5 mmol) in CH2Cl2 (20 mL) at room temperature under nitrogen was added N-methylmorpholine (1.65 mL, 15 mmol). After stirring at room temperature for 18 hrs, the mixture was partitioned between EtOAc-water. The organic phase was washed with 5% KHSO4, saturated NaHCO3 and saturated NaCl solutions, dried over anhydrous Na2SO4 and evaporated to give the title compound (5.56 g, 99%) as viscous oil. TLC(EtOAc-hexane; 1:1) Rf=0.48.
99% With 4-methyl-morpholine; In dichloromethane; Part A [(N-Benzyloxycarbonyl)Leucinyl]Aspartic Acid, beta-tert-Butyl, alpha-Methyl Ester To a solution of (N-benzyloxycarbonyl)leucine, N-hydroxysuccinimide ester (4.54 g, 12.5 mmol) and aspartic acid, beta-tert-butyl, alpha-methyl ester hydrochloride (3.00 g, 12.5 mmol) in CH2Cl2 (20 mL) at room temperature under nitrogen was added N-methylmorpholine (1.65 mL, 15 mmol). After stirring at room temperature for 18 hrs, the mixture was partitioned between EtOAc-water. The organic phase was washed with 5% KHSO4, saturated NaHCO3 and saturated NaCl solutions, dried over anhydrous Na2SO4 and evaporated to give the title compound (5.56 g, 99%) as viscous oil. TLC(EtOAc-hexane; 1:1) Rf=0.48.
Reference： [1]Patent: US6197750,2001,B1
[2]Patent: US6242422,2001,B1
  • 34
  • [ 38862-25-8 ]
  • poly(N-methacryloxysuccinimide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: methacrylic acid N-hydroxysuccinimide ester With [2,2]bipyridinyl In dimethyl sulfoxide for 0.0833333h; Stage #2: With 2-hydroxyethyl 2-bromoisobutyrate In dimethyl sulfoxide at 100℃; A2 Homogeneous polymerisation : This reaction is shown in Scheme 2. In a typical copper mediated polymerisation using DMSO as solvent at the preferred weight concentration of 56% in monomer 3, copper (I) bromide (31.3 mg, 0.2 mmol), 2-2'- bipyridine (Bpy) (68.3 mg, 0.4 mmol) and monomer 3 (2.00 g, 10.9 mmol) were added to a round bottomed flask which was then sealed with a septum. Into the flask was then injected DMSO (1.3 g). The resulting brown mixture was gently heated until a solution had formed and then purged with argon for approximately 5 min. An argon purged solution of 2-bromo-2-methyl- (2-hydroxyethyl) propaneate 4 (46.1 mg, 0.2 mmol) in DMSO (0.2 g) was then injected into the mixture and the flask was heated to 100 °C in an oil bath. The reaction mixture became viscous after a few minutes and was removed from the heat after 10-15 minutes and rapidly cooled. The polymeric product was isolated by addition of 7-8 ml of DMSO to dissolve the crude product mixture which was slowly added to a stirred solution of acetone (100 ml) to precipitate PMOSu 1 as a white solid. The acetone solution turned a green colour during the precipitation of polymer 1 due to the dissolution of copper species and the ligand. Atomic absorption analysis indicated the copper content in polymer 1 when at a concentration of 28.0 mg/ml in DMF to be 0.153 ppm. Precipitation of polymer 1 from the DMSO reaction solution into acetone may offer a viable alternative to alumina chromatography that has been typically used in copper mediated polymerisations to remove copper from the product polymer. The isolated yield of polymer 1 was 1.78 g (89%). The number average molecular weight was 22,700 g/mol and polydispersity index was 1.20. Apparent molecular weights and molecular weight distributions for PMOSu 1 were determined using Waters Styragel HR4 and HR3 (7.3 x 300 mm) columns coupled to a Gibson 133 refractive index detector, poly (methyl methacrylate) PMMA calibration standards and DMF with 0. 1% LiCI eluent
80% With 4,4'-dicyano-4,4'-azo-di-valeric acid In acetone at 70℃; for 3.5h; A.6 Synthesis of PMOSu 1 by free radical polymerization with 4, 4'- azobis (cyanovaleric acid) followed by hydrolysis to give PMAA-Na 2. A pressure tube was charged with methacryloxysuccinimide 3 (0.5-1. 0 g), and 4,4'-azobis (cyanovaleric acid) (15-30 wt%) and solvent (for example acetone, freshly distilled THF, or mixtures of these solvents including toluene and ethylene carbonate) and the resulting solution was sealed and purged with argon for 15 min. The sealed flask was then heated at 70-120 °C for 0.25-2. 5 h. See Table 4 for the conditions of example reactions. PMOSu 1 was isolated as a white precipitate by filtration and dried in vacuo and GPC determined in DMF using PMMA standards.
39% With [2,2]bipyridinyl; 2-bromo-2-methylpropionic acid; copper(I) bromide In [1,3]-dioxolan-2-one A2 Precipitation polymerisation : Copper mediated polymerisations of monomer 3 in solvents such as THF, ethyl acetate, toluene and acetone also gave narrow MWD polymer 1. Yields ranged from 10-95 % depending on the polymer mole- cular weight. Higher molecular weight polymer 1 up to 25,000 g/mol was obtained in mixed solvent systems such as THF and ethylene carbonate. At molecular weights above 10,000 g/mol the yields were sometimes less than that observed when the polymerisation was conducted in DMSO or DMF. Exemplary copper mediated polymerisations using 0.5 g in monomer 1 were conducted in THF over a 16 h time period at 70 °C and are listed in Table 2. The copper chelating legend used in these THF reactions was N, N, N', N", N"-pentamethyldiethylenetriamine (PMDETA). Additional precipitation reactions are listed in Table 3 with 2-bromo-2- methyl propionic acid (BMA) used as initiator
With 2,2'-azobis(isobutyronitrile) In acetone at 50℃; for 24h; A5 An argon purged solution of methacryloxy succinimide 3 (3 g) and AIBN (0.135 g) in acetone (30.0 ml) was heated at 50°C in a closed vessel for 24 h. The white precipitate formed was isolated by filtration, dissolved in DMSO (6.0 ml) and re- precipitated in rapidly stirring acetone. After isolating by filtration and drying in- vacuo, some of the dried PMOSu 1 (0.48 g) in DMSO (4.8 ml) was mixed with 1 N sodium hydroxide (5.2 ml) and water (56 ml). The resulting solution was allowed to stir for 1 h at room temperature whereupon it was diluted to 105 mL with fresh water and dialysed against 5 L of water for 24 h using a Visking dialysis mem- brane (MWCO 7000, Medicell International). The 5 L of water was changed 6 times. The dialysed solution was filtered though a 0. 2 um filter and then freeze- dried to afford PMAA-Na 2 (0.56 g) as a solid product; Mw 26,100 Da, Mn 15,200 g/mol, Mw/Mn 1.7 (SEC 0.2 M aqueous NaN03/10% CH3CN, PMAA-Na standards)

Reference： [1]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 55-56
[2]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 60
[3]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 57-58
[4]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 60
  • 35
  • [ 38862-25-8 ]
  • PEG-2000 macroinitiators [ No CAS ]
  • PEG-PMOSu [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: methacrylic acid N-hydroxysuccinimide ester With [2,2]bipyridinyl; copper(I) bromide In [1,3]-dioxolan-2-one for 0.25h; Stage #2: PEG-2000 macroinitiators In [1,3]-dioxolan-2-one at 80℃; for 1h; B.C Copper (l) bromide (31.2 mg, 0.2 mmol), bpy (68.4 mg, 0.4 mmol) and N- methacryloxysuccinimide 3 (3.67 g, 20 mmol) and ethylene carbonate (2 g) were added to a round-bottomed flask that was then sealed with a septum. The resulting brown mixture was gently heated until a solution had formed and then purged with argon for approximately 15 min. An argon-purged solution of PEG2000-macroinitiator 5 (430 mg, 0.2 mmol) in ethylene carbonate (0.6 g) was then injected into the mixture and the flask was heated to 80 °C in an oil bath for 1 h. The viscous reaction mixture was then removed from the heat and rapidly cooled. The resulting crude polymeric product was dissolved in DMF (8 ml) and the resulting solution was slowly added to stirred methanol (500 ml) to precipitate PEG-PMOSu 6 as a white solid (3.8 g, 92%); Mn = 37,160 g-mol-1 Mw/Mn = 1.32 SEC (DMF 0. 1% LiCI). 1H NMR (DMSO-d6) 8 1. 38 (br, 3H, CH3), 2.42 (br m, 2H, CH2C), 2.78 (br, 4H, CH2CH2), 3.50 (s, 4H, OCH2CH20).
56% Stage #1: methacrylic acid N-hydroxysuccinimide ester With [2,2]bipyridinyl; copper(I) bromide In [1,3]-dioxolan-2-one for 0.583333h; Stage #2: PEG-2000 macroinitiators In [1,3]-dioxolan-2-one at 80℃; for 1.5h; B.B mixture of monomer 3 (as synthesised in WO 01/18080), ethylene carboate and bipyridine was placed in a tube sealed with a septum and it was purged with argon for 5 minute and the CuBr was added. The misture was gently heated to form a solution (deep brown in colour) and purged with argon for another 30 minutes. Then a solution of the PEG macroinitiator 5 in the amount relative to the monomer specified in Table 5 in ethylene carbonate (gently heated to liquidfy both the ethylene carbon and 5) was purged with argon for 10 minutes and added to the monomer solution by syringe washed with argon. The mixture was placed in an oil bath and stirred. The reaction was stopped by exposure to air, cooling and diluting with DMF. Then the solution was passed through a column filled with alumina and the polymer precipitated in methanol. The PEG-PMOSu 6 precipitate was filtered, washed with ether and dried in vacuum. The PEG-PMOSu 6 was obtained as a white powder. Table 5 show polymerisation conditions, yield and molecular weight characteristics of polymerisation conducted with microinitiator 5 derived from PEG of molecular weight 2000 g/mol
Reference： [1]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 63-64
[2]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 62-63
  • 36
  • [ 38862-25-8 ]
  • PEG-5000 macroinitiators [ No CAS ]
  • PEG-PMOSu [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With [2,2]bipyridinyl; copper(I) bromide In [1,3]-dioxolan-2-one at 110℃; for 2h; B.D Copper (l) bromide (10.4 mg, 0.072 mmol), 2,2'-bipyridine (bpy, 22.6 mg, 0.145 mmol), and N-methacryloxysuccinimide (2.0 g, 10.8 mmol), and PEG5000- macroinitiator 5 (362 mg, 0.072 mmol) and ethylene carbonate (2.362 g) were added to a Schlenk flask which was then sealed with a septum. The resulting brown mixture was degassed by freeze thaw method. The mixture was heated to 110°C in an oil bath for 2 h. The viscous reaction mixture was then removed from the heat and rapidly cooled. The resulting crude polymeric product was then dissolved in DMF (8 ml). The resulting solution was slowly added to stirred methanol/diethylether (2: 1 v/v, 300 ml) to precipitate PEG-PMOSu 6 as a white solid (1.8 g, 76%). Mn = 32,860 gNo.mol-1 Mw/Mn = 1.36 (SEC (DMF 0. 1% LiCl). 1H NMR (DMSO-d6) 8 1.38 (br, 3H, CH3), 2.42 (br m, 2H, CH2C), 2.78 (br, 4H, CH2CH2), 3.50 (s, 4H, OCH2CH20).
Reference： [1]Current Patent Assignee: WELSH, CARSON, ANDERSON & STOWE - WO2005/65712, 2005, A2 Location in patent: Page/Page column 64
  • 37
  • [ 6066-82-6 ]
  • 25-hydroxyvitamin D3-3-hemisuccinate [ No CAS ]
  • [ 1892-57-5 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
94% With sodium sulfate; In dichloromethane; 10.0 mg (20 mumol) 25-hydroxyvitamin D3-3-hemisuccinate was dissolved in 7 ml anhydrous dichloromethane and admixed with 2.76 mg (24 mumol) N-hydroxysuccinimide and 3.72 mg (24 mumol) N(3-dimethylaminopropyl)-N'-ethyl-carbodiimide (EDC). It was stirred overnight under argon, the organic phase was then washed twice with 10 ml water, dried over about 1 g anhydrous sodium sulfate and filtered. The solvent was removed in a vacuum and the residual reaction product was dried for 3 h in a high vacuum. 11.3 mg (yield: 94%) N-hydroxysuccinimide ester was obtained which was used for the conjugation without further purification.
Reference： [1]Patent: US2009/93445,2009,A1
  • 38
  • [ 38862-25-8 ]
  • [ 13749-61-6 ]
  • poly(N-(methacryloyloxy)succinimide-co-N-isopropylmethacrylamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.6% With 2,2'-azobis(isobutyronitrile); In tert-butyl alcohol; at 80℃; for 20.0h; N-(Methacryloyloxy)succinimide (2.745 g; 15 mmol), N-isopropylmeth-acrylamide (19.05 g; 150 mmol) and AiBN (83.9 mg; 0.5 mmol) were stirred in degassed tert-butanol (100 ml) under argon at 80 C. for 20 hours. The precipitate was filtered off and the filtrate was dropped slowly in hexane (1.8 1) to precipitate the polymer. The product was isolated by filtration. Yield: 13.2 g (60.6%) after drying in high vacuum.
Reference： [1]Patent: US2005/101813,2005,A1 .Location in patent: Page/Page column 32
  • 39
  • [ 38862-25-8 ]
  • [ 1569904-93-3 ]
  • [ 1569904-98-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane 5 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepin-7-yl)methyl)hexanamide Example 5 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepin-7-yl)methyl)hexanamide To a solution of (2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[b]thieno[2,3-e][1,4]diazepin-7-yl)methanamine, prepared as described in Example 3, (59 mg, 0.17 mmol) in dichloromethane (4 mL) was added triethylamine (0.048 mL, 0.34 mmol) and 6-maleimidohexanoic N-hydroxysuccinimide ester (53 mg, 0.17 mmol) in dichloromethane (1 mL). The solution was stirred at room temperature for 40 min, then loaded onto a silica column, eluted with 3-5% methanol/dichloromethane containing triethylamine. The title compound was obtained as a yellow solid. LC-MS: m/z 535 (M+1).
Reference： [1]Current Patent Assignee: SALADAX BIOMEDICAL, INC. - US2014/57303, 2014, A1 Location in patent: Page/Page column
  • 40
  • [ 38862-25-8 ]
  • [ 1569089-98-0 ]
  • [ 1569089-99-1 ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine In acetonitrile at 20℃; for 24h;
Reference： [1]Xu, Zhangyan; Lai, Junping; Tang, Rupei; Ji, Weihang; Wang, Rui; Wang, Jun; Wang, Chun [Macromolecular Bioscience, 2014, vol. 14, # 7, p. 1015 - 1024]
  • 41
  • [ 38862-25-8 ]
  • 2-[(4-[(2-methoxy-1,3-dioxolan-4-yl)methoxy]methyl}-1,3-dioxolan-2-yl)oxy]ethan-1-amine [ No CAS ]
  • N-{2-[4-(2-methoxy-[1,3]dioxolan-4-ylmethoxymethyl)-[1,3]dioxolan-2-yloxy]ethyl}methacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With triethylamine In acetonitrile Darkness;
With dmap In tetrahydrofuran at 20℃; 1.3 N- {2- [2-methoxy- [1,3] dioxolane - 4- (2-methoxy- [1,3] Dioxolane-4-methyleneoxy) ] -ethyl} -2_ Methacrylamide of preparation A solution of 2- [2_methoxy- [1,3] dioxolane-4- (2-methoxy- [1,3] dioxolan-4-methyleneoxy] N-succinimidyl methacrylate and 4-dimethylaminopyridine were dissolved in acetonitrile in a molar ratio of 1: (1-1.1): 1, and the reaction was carried out at room temperature for 24-48 hours. After removal of acetonitrile by evaporation, Ethyl acetate was added and the mixture was washed with aqueous sodium carbonate and the crude product was chromatographed on silica gel (eluent: ethyl acetate) to give N- {2- [2-methoxy- [1,3] dioxane (2-methoxy- [1,3] dioxolane-4-methyleneoxy)] - ethyl} -2'-methacrylamide monomer
Reference： [1]Zhou, Xiaojing; Luo, Shi; Tang, Rupei; Wang, Rui; Wang, Jun [Macromolecular Bioscience, 2015, vol. 15, # 3, p. 385 - 394]
[2]Current Patent Assignee: ANHUI UNIVERSITY - CN104151284, 2016, B Location in patent: Paragraph 0045-0046
  • 42
  • [ 38862-25-8 ]
  • [ 123628-75-1 ]
  • 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl(2-methacrylamidoethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Synthesis of cholesteryl monomer (7) (10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl(2methacrylamidoethyl)carbamate) (7). A solution of 6 (100 mg,0.54 mmol) in dry dichloromethane/DMF (1/1, 15 ml) undernitrogen was treated with 3 (258 mg, 0.54 mmol). The reactionmixture was stirred for 1 h at room temperature and the solventremoved under reduced pressure. Ethyl ether (60 ml) was added tothe residue, washed with water (3x10 ml), brine (2x10 ml), driedover sodium sulphate and concentrated to dryness. Purification bysilica gel chromatography eluting with 1:1 Exane/EtOAc gave 7 as awhite solid (243 mg, 82%).
Reference： [1]Martin, Chloe; Marino, Nino; Curran, Ciara; McHale, Anthony P.; Callan, John F.; Callan, Bridgeen [International Journal of Pharmaceutics, 2016, vol. 511, # 1, p. 570 - 578]
  • 43
  • [ 6066-82-6 ]
  • [ 79-41-4 ]
  • [ 38862-25-8 ]
YieldReaction ConditionsOperation in experiment
86% With dicyclohexyl-carbodiimide In acetonitrile at 25℃; Inert atmosphere; Synthesis of intermediate compound 2,5-dioxopyrrolidin-1-ylmethacrylate (6) To a 25 ml round-bottomflask were added 100 mg ofmethacrylic acid (4) (1.16 mmol), 160 mg of N-hydroxysuccinimide(5) (1.39 mmol), and 598 mg of dicyclohexylcarbodiimide(2.9 mmol). After 8 ml of dry acetonitrile was injected, the mixturewas stirred under nitrogen for about 16-24 h at 25 C. The wholeprocess was monitored by TLC. After reaction, the suspension wasfiltered and the solution was evaporated by rotavapor under highlyreduced pressure. The residue was purified by silica columnchromatography (Exane/EtOAc, gradient from 4:1 to 3:2). Theobtained compound was recrystallized from EtOAc and produced200 mg of white powder (6). Yield: 86%.
75% With dicyclohexyl-carbodiimide In ethyl acetate at 0 - 20℃;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 4℃; 1 Methacrylic acid (9.0 g, 0.1 mole) and N-hydroxysucinimide (11.5 g, 0.1 mole) were placed in a round bottom flask and dissolved in 300 mE of THF. The solution was cooled in an ice bath. Dicyclohexyl carbodiimide (21.0 g, 0.1 mole) dissolved in SOmE THF was added. The reaction mixture was stirred for 2 hrs in an ice bath.
Reference： [1]Martin, Chloe; Marino, Nino; Curran, Ciara; McHale, Anthony P.; Callan, John F.; Callan, Bridgeen [International Journal of Pharmaceutics, 2016, vol. 511, # 1, p. 570 - 578]
[2]Wickramasinhage, Ravindra N.; Goswami, Shailesh K.; McAdam, C. John; Malik, Sharali; Hanton, Lyall R.; Moratti, Stephen C. [RSC Advances, 2019, vol. 9, # 57, p. 33187 - 33192]
[3]Current Patent Assignee: SIEMENS AG - US2016/340541, 2016, A1 Location in patent: Paragraph 0315
  • 44
  • [ 38862-25-8 ]
  • C28H27FN8O2 [ No CAS ]
  • C32H31FN8O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 20℃; Synthesis of Compound 7: Synthesis of Compound 7: To a solution of intermediate 10-b (80 mg, 0.12 mmol) in DMF (1.3 ml) were sequentially added TEA (219 μΙ, 1.6 mmol) and 2,5-dioxopyrrolidin-l-yl methacrylate (35 mg, 0.18 mmol) and the reaction was then stirred at room temperature overnight. Brine and ethyl acetate were added; the organic layer was separated, dried over MgS04, filtered and concentrated under reduced pressure. Purification by silica gel chromatography provided Compound 7 as a beige solid.
Reference： [1]Current Patent Assignee: GOSSAMER BIO INC - WO2016/187723, 2016, A1 Location in patent: Page/Page column 71
  • 45
  • [ 38862-25-8 ]
  • [ 22483-09-6 ]
  • [ 95984-11-5 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine In tetrahydrofuran at 20℃; for 72h; 1 Synthesis of MAMDMA Methacrylic acid (9.0 g, 0.1 mole) and N-hydroxysucinimide (11.5 g, 0.1 mole) were placed in a round bottom flask and dissolved in 300 mL of THF. The solution was cooled in an ice bath. Dicyclohexyl carbodiimide (21.0 g, 0.1 mole) dissolved in 50 mL THF was added. The reaction mixture was stirred for 2 hrs in an ice bath. Aminoacetaldehyde dimethyl acetal (15.0 g, 0.1 mole) and triethylamine (15.0 g, 0.15 mole) were added. The reaction mixture solidified to a cake and became difficult to stir due to this addition. An additional 300 mL THF was added. The reaction mixture was warmed up to room temperature and stirred for 3 days. Reaction mixture was filtered to remove precipitated solids. The clear solution was concentrated under reduced pressure. MAMDMA was obtained as a viscous liquid. Yield: 20.0 g, 90%. 1H NMR (CDCl3): 5.4 δ 1H, 5.6 δ 1H (double bond protons), 3.5 δ 6H (acetal protons) 3.1 δ 1H (-CH-(OCH3)2), 2.5 δ 2H (-CH2-CH-), 2.3 δ 1H (-NH-), 1.8 δ 3H (═C-CH).
Reference： [1]Current Patent Assignee: SIEMENS AG - US2016/340541, 2016, A1 Location in patent: Paragraph 0315
  • 46
  • [ 38862-25-8 ]
  • C97H193BrO48 [ No CAS ]
  • C127H225BrN4O63 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With N-propyl 2-pyridylmethanimine; copper(I) bromide In dimethyl sulfoxide at 70℃; for 24h;
Reference： [1]Yin, Hongyao; Feng, Yujun [RSC Advances, 2016, vol. 6, # 83, p. 79943 - 79951]
  • 47
  • [ 38862-25-8 ]
  • C12H13NO4 [ No CAS ]
  • C16H17NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With triethylamine In acetonitrile at 0 - 20℃; for 16h; 1.f Step f: Preparation of compound 7 (f reaction for preparing compound 7 represented by 7 in scheme 1) The compound 6 (0.44 g, 1.3 mmol) was dissolved in anhydrous acetonitrile (6.6 mL) and then triethylamine (0.22 mL, 1.6 mmol).And Succinimidyl methacrylate (0.27 g, 1.5 mmol) was added. After cooling to 0° C., the mixture was stirred at room temperature for 16 hours. Then, 0.01 M HCl was added and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 solution, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification by silica gel flash column chromatography gave compound 7 as a light yellow solid. (0.23 g, 59% yield)
Reference： [1]Current Patent Assignee: SEOUL NATIONAL UNIVERSITY - KR2020/37114, 2020, A Location in patent: Paragraph 0133; 0135; 0146; 0147
  • 48
  • [ 38862-25-8 ]
  • C21H24N4O5S [ No CAS ]
  • C25H28N4O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With triethylamine In dimethyl sulfoxide The resulting intermediate HB7-Cys (3 g, 6.76 mmol) was dissolved in anhydrous DMSO (20 mL) in the presence of triethylamine (1.9 mL, 2.2 eq., 14.87 mmol). N- hydroxysuccinimidyl methacrylate or NHS-MA (CAS: 38862-25-8, 1.28 g, 1.2 eq., 8.12 mmol) was pre-dissolved in DMSO (3 mL) and added subsequently to the reaction mixture. Methacryloyl chloride could be used as an alternative to NHS-MA, however, side reaction would likely occur due to high reactivity of the reagent. The emergence of methacrylamide peaks at 5.7, 5.36 and 4.4 ppm indicated successful re-attachment of the polymerisable group to the cysteine moiety. The integration of the benzotriazole proton from HB-7 at 7.84 ppm (2 protons) compared to the methacrylamide proton at 5.30 ppm (1 proton) indicated that about 1:1 molar attachment of methacrylamide linker to the hydroxyphenyl- benzotriazole moiety. For purification the reaction mixture was diluted in DCM, followed by washing with water (brine solution can be added to break the emulsion). The organic phase was dried over MgSCL, followed by solvent removal under vacuum. The resultant product HB7-Cys-MA was purified using column chromatography (15% v/v methanol in dichloromethane) to give about 1.8 g white- off solid (yield: 51%). The ESI-MS showed a mass of 511.1648 m/z (-H) and 535.1622 m/z (+Na). The attachment of cysteine allowed the polymerisable UV absorber to exhibit a carboxylic acid (anionic) group in its linker. HB7-Cys-MA was also found to be soluble in basic aqueous and brine solutions.
Reference： [1]Current Patent Assignee: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION - WO2020/118361, 2020, A1 Location in patent: Page/Page column 50; 51
  • 49
  • [ 38862-25-8 ]
  • C21H23NO7S [ No CAS ]
  • C25H27NO8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With triethylamine In dimethyl sulfoxide The resulting intermediate BP15-Cys (2 g, 4.61 mmol) was dissolved in anhydrous DMSO (15 mL) in the presence of triethylamine (1.3 mL, 2.2 eq., 1.01 mmol). N-hydroxysuccinimidyl methacrylate or NHS-MA (CAS: 38862- 25-8, 1.1 g, 1.3 eq., 6.00 mmol) was pre-dissolved in DMSO (5 mL) and added subsequently to the reaction mixture. The emergence of methacrylamide peaks at 5.8, 5.3 and 4.4 ppm indicated successful re-attachment of the polymerisable group to the cysteine moiety. The integration of the benzophenone proton from BP15 at 6.47 ppm (1 proton) compared to the methacrylamide proton at 1.9 ppm (3 protons) indicated that about 1:1 molar attachment of methacrylamide linker to the benzophenone moiety. For purification the reaction mixture was diluted in DCM, followed by washing with water (brine solution can be added to break the emulsion). The organic phase was dried over MgSCL, followed by solvent removal under vacuum. The resultant product BP15-Cys-MA was purified using column chromatography (15% v/v methanol in dichloromethane) to give about 0.6 g white yellowish solid (yield: 26%). The ESI-MS showed a mass of 500.138 m/z (-H) and 524.1356 m/z (+Na).
Reference： [1]Current Patent Assignee: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION - WO2020/118361, 2020, A1 Location in patent: Page/Page column 56
  • 50
  • [ 38862-25-8 ]
  • C21H17NO4 [ No CAS ]
  • N-(2-(4-(3-hydroxy-4-oxo-4H-benzo[g]chromen-2-yl)phenoxy)ethyl)methacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.35 g With trifluoroacetic acid In chloroform at 20℃; for 12h;
Reference： [1]Cheng, Jian; Gan, Guihai; Gao, Lei; Hu, Jinming; Shen, Zhiqiang; Zhang, Guoying [Angewandte Chemie - International Edition, 2021, vol. 60, # 24, p. 13513 - 13520][Angew. Chem., 2021, vol. 133, # 24, p. 13625 - 13632,8]
  • 51
  • [ 38862-25-8 ]
  • C17H15NO4 [ No CAS ]
  • N-(2-(4-(3-hydroxy-4-oxo-4H-chromen-2-yl)phenoxy) ethyl)methacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.77 g With trifluoroacetic acid In chloroform at 20℃; for 12h;
Reference： [1]Cheng, Jian; Gan, Guihai; Gao, Lei; Hu, Jinming; Shen, Zhiqiang; Zhang, Guoying [Angewandte Chemie - International Edition, 2021, vol. 60, # 24, p. 13513 - 13520][Angew. Chem., 2021, vol. 133, # 24, p. 13625 - 13632,8]

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