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[ CAS No. 23911-26-4 ] {[proInfo.proName]}

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Chemical Structure| 23911-26-4
Chemical Structure| 23911-26-4
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Product Details of [ 23911-26-4 ]

CAS No. :23911-26-4 MDL No. :MFCD00010697
Formula : C14H19N3O8 Boiling Point : -
Linear Structure Formula :HO2CCH2N(C2H4N(CH2CO)2O)2 InChI Key :RAZLJUXJEOEYAM-UHFFFAOYSA-N
M.W : 357.32 Pubchem ID :100825
Synonyms :
Chemical Name :Diethylenetriaminepentaacetic dianhydride

Calculated chemistry of [ 23911-26-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.64
Num. rotatable bonds : 8
Num. H-bond acceptors : 11.0
Num. H-bond donors : 1.0
Molar Refractivity : 86.44
TPSA : 133.76 Ų

Pharmacokinetics

GI absorption : Low
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) : -10.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : -3.33
Log Po/w (WLOGP) : -3.62
Log Po/w (MLOGP) : -1.92
Log Po/w (SILICOS-IT) : -1.01
Consensus Log Po/w : -1.72

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.57
Solubility : 1330.0 mg/ml ; 3.72 mol/l
Class : Highly soluble
Log S (Ali) : 1.1
Solubility : 4450.0 mg/ml ; 12.5 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.5
Solubility : 114.0 mg/ml ; 0.318 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.63

Safety of [ 23911-26-4 ]

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 [ 23911-26-4 ]

* 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.

  • Downstream synthetic route of [ 23911-26-4 ]

[ 23911-26-4 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 23911-26-4 ]
  • [ 143-27-1 ]
  • [ 144605-35-6 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: diethylenetriaminepentaacetic dianhydride; hexadecylamine In chloroform; N,N-dimethyl-formamide at 40℃; for 24h; Stage #2: With water at 80℃; for 1h;
61.2% In chloroform; N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere; Synthesis of DTPA-BA (3a-c) General procedure: Under a N2 atmosphere, 2 (0.50 g, 1.40 mmol) in anhydrousdimethyl formamide (DMF) was heated to 85 C.After the solid was entirely dissolved, the system temperaturewas cooled to 40°C and then dodecanamine (0.57 g,3.08 mmol) dissolved in trichloromethane was added to thesolution dropwise. The mixture was stirred for 2 h. Aftercooling and filtering, the residue was dissolved in 1 MNaOH, and then filtered again. The filtrate was adjusted topH 2-3 by adding 1 M HCl, filtered, and then the residuewas dried in vacuo overnight. The solid was recrystallizedfrom anhydrous EtOH and then dried in vacuo overnight.3b was recrystallized from a mixture of MeOH and chloroform,and 3c from n-butylalcohol.
52% In chloroform; N,N-dimethyl-formamide at 40℃; for 2h;
In chloroform; N,N-dimethyl-formamide for 12h;

  • 2
  • [ 67-43-6 ]
  • [ 23911-26-4 ]
YieldReaction ConditionsOperation in experiment
97% With pyridine; acetic anhydride; at 65℃; for 3h; a) Preparation of <strong>[67-43-6]diethylenetriaminopentaacetic acid</strong> bis-anhydride <strong>[67-43-6]diethylenetriaminopentaacetic acid</strong> (10 g; 0.0255 mol) and pyridine (14.54 ml; 0.18 mol) are charged into a 100-ml reaction flask equipped with magnetic stirrer, heating oil bath, and dripping funnel.. While the temperature is kept at the room value and the solution is stirred, acetic anhydride (10.56 ml; 0.11 mol) is added dropwise.. The reaction mixture is heated to 65 C for 3 hours, and then cooled to room temperature.. The solid obtained is recovered by filtration on buechner, washed on filter with acetic anhydride (2 x 10 ml), methylene chloride (2 x 10 ml) and ethyl ether (2 x 10 ml).. The white powder is then dried under vacuum yielding 8.82 g of the compound of title a) (97 %).
97% With pyridine; acetic anhydride; In acetonitrile; at 60℃; for 4h;Large scale; Diethylenetriamine pentaacetic acid (2029 g, 5.16mole) was dissolved in acetonitrile (1100 mL) with agitation. Acetic anhydride (1450 mL, 15.3 mole) and pyridine (1660 ml, 20.5 mole) were added and the reaction was heated to 60C for 4 hours. The reaction mixture was cooled to 22C and t-butylmethylether (MTBE) (800 mL) was added. The reaction mixture was filtered and the solid obtained was washed with MTBE (3000 mL). The solid was dried in a vacuum oven at 40C. Yield: 1792 g, 97%
95.9% With pyridine; acetic anhydride; In acetonitrile; at 60℃; for 18h;Heating / reflux; <strong>[67-43-6]Diethylenetriaminepentaacetic acid</strong> (1006 g, DTPA, Aldrich), acetonitrile (391.94 g, EMD Chemicals), acetic anhydride (777.23 g, Mallinckrodt), and pyridine (900.96 g, Mallinckrodt) were added, in that order, to a 5 L reaction flask, equipped with an overhead stirrer, a temperature probe, and a reflux condenser. The flask was placed on a heating mantle, and the reaction mixture was heated to 6O0C and refluxed at that temperature for 18 hours.[0053] The mixture was allowed to cool to below 45C. Cooling, which took about 1.5 hours, caused the formation of a precipitate. The solids were isolated by vacuum filtration, and the product was washed, first with isopropyl alcohol (3249 g), and next with acetonitrile (3501 g). The washed solid cake was dried at 45C to 500C under 22 mmHg vacuum for 18 hours.[0054] A total of 873.2 g DTPA bis-anhydride was synthesized by this reaction, representing a 95.9% yield based on DTPA starting material. The DTPA bis-anhydride purity was 100% as determined by gas chromatography.
85.9% With pyridine; acetic anhydride; at 65℃; for 24h;Inert atmosphere; DTPA (1) (2.00 g, 5.08 mmol) in anhydrous acetic anhydride(2.5 mL, 26.4 mmol) and anhydrous pyridine(3.5 mL, 43.4 mmol) was stirred under a N2 atmosphere at65 C for 24 h. After cooling to room temperature, thereaction mixture was washed with anhydrous acetic anhydrideand anhydrous diethyl ether repeatedly. The solventswere removed under vacuum to yield a light yellow solid.Yield (1.56 g, 85.9%), m.p. 178-188C.
83.2% With pyridine; acetic anhydride; at 65℃; for 24h;Inert atmosphere; Add 2g DTPA, 2.5mL anhydrous acetic anhydride, 3.5mL anhydrous pyridine to 50mLIn a single-necked flask, heated under reflux with nitrogen at 65 C for 24 h.The dark brown suspension was obtained, suction filtered, and the filter cake was washed with anhydrous acetic anhydride and anhydrous diethyl ether to afford colorless, and dried under vacuum at 80 C for 12 h to give 1.51 g of white solid and the yield is 83.2%.
78% With acetic anhydride; In pyridine; at 65℃; for 24h; 10.0 g (25 mmol) of DTPA was dispersed in 20 ml of pyridine. 18 g (0.18 mol) of acetic anhydride was added to the dispersion, and a reaction was allowed to take place at 65C for 24 hrs with stirring. After the reaction was completed, the reaction mixture was filtered to recover generated material. The recovered compound was washed with acetic anhydride and diethyl ether several times, and dried under pressure for 24 hrs, thereby obtaining a DTPA anhydride at a yield of 78%. IR(cm-1) 2979, 1820, 1774, 1641.
78% With acetic anhydride; In pyridine; at 65℃; for 24h; 10.0 g (25 mmol) of DTPA was dispersed in 20 ml of pyridine. 18 g (0.18 mol) of acetic anhydride was added to the dispersion, and a reaction was allowed to take place at 65 for 24 hrs with stirring. After the reaction was completed, the reaction mixture was filtered to recover generated material. The recovered compound was washed with acetic anhydride and diethyl ether several times, and dried under pressure for 24 hrs, thereby obtaining a DTPA anhydride at a yield of 78%. IR(cm-1) 2979, 1820, 1774, 1641. Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of 3-amino-2,4,6-triiodobenzoic acid, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.802.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243.
75% With pyridine; acetic anhydride; at 64.84℃; for 5h;Inert atmosphere; Acetic anhydride (4.90 mL, 51.72 mmol) and dry pyridine(6.30 mL, 77.52 mmol) were added, in a three neck flask, todiethylenetriaminepentaacetic acid (DTPA, 5.08 g, 12.92 mmol) andthe reaction mixture was left on stirring under nitrogen at T = 338 Kfor 5 h. Then it was filtered and the solid white product was washedwith acetic anhydride (3 × 10 mL) and dry ACN (3 × 10 mL) anddried at about T = 313 K, to afford the title compound (3.46 g, eta =75%). 1H NMR (400 MHz, methanol-d4), delta (ppm): 3.98 (8H, s,CH2COOCO), 3.70 (2H, s, CH2COOH), 3.41 (4H, t, CH2CH2NCH2COOH),3.25 (4H, t, CH2CH2NCH2COOH). FT-IR (KBr, Fig. S1), wavenumber(cm-1): 1820 (asymmetric C_O stretching anhydride), 1776(symmetric C_O stretching anhydride), 1640 (C_O stretching carboxylicacid), 1332 (CO stretching), 1112 (CN stretching), 955 (OHbending).
With pyridine; acetic anhydride; at 65℃; for 24h; DTPA-di-anhydrade: <strong>[67-43-6]Diethylenetriaminepentaacetic acid</strong> (39.3g, 0.1 mole) was suspended in pyridine (50g), and acetic anhydride (40.8g. 0.4 mole) was added. The mixture was heated at 65C for 24 hours. The product was filtered, washed with acetic anhydride and ether, and dried.
With pyridine; acetic anhydride; at 65℃; for 24h; Weighing dtpa 7.8100g (0.02mmol), acetic anhydride 16.0 ml (0.08mmol), pyridine 10.0 ml (0.12mmol) is placed in the three-necked round-bottom flask, in the 65 C under slow stirring and heating 24h. Cooling to room temperature, the reaction mixture is filtered, and a small amount of anhydrous ethyl ether washing twice, using the vacuum pump suction, the resulting calculator in the vacuum drying box 80 C vacuum drying, to obtain dtpaa.
With pyridine; acetic anhydride; at 80℃; for 12h; 1) 7.8462g, 0.02mmol of DTPA, 6mL of acetic anhydride, was dissolved in 8 mL of pyridine in 50mL round bottom flask, at reflux temperature 80 C for 12h, cooled to room temperature, filtered off with suction, washed twice with small amount of ether to It was washed twice with 10 mL of acetic anhydride and finally with a small amount of diethyl ether to obtain a relatively pure white product, diethylenetriamine pentaacetic anhydride (DTPAA)
With pyridine; acetic anhydride; at 65℃; for 24h; Weigh 7.8670g (0.02mol) of diethylenetriaminepentaacetic acid (dtpa), acetic anhydride 16.0mL (0.08mol), pyridine 10.0mL (0.12mol) in a three-necked round bottom flask, stir slowly at 65 C , condensed reflux for 24h. The heating and stirring were stopped, and after cooling to room temperature, the product was filtered under reduced pressure, washed three times with acetic anhydride and anhydrous diethyl ether (3×10 mL), and filtered under reduced pressure. The product was dried at 60 C in a dry box. Diethylenetriamine pentaacetic acid dianhydride (dtpaa) was obtained.
With pyridine; acetic anhydride;Inert atmosphere; Reflux; <strong>[67-43-6]Diethylenetriaminepentaacetic acid</strong>,Anhydrous acetic anhydride and anhydrous pyridine are added to a single-necked flask.Under nitrogen protection, heat to reflux, after 12 to 24 hours of reaction,Filter by suction and wash the filter cake to colorless.Vacuum drying at 50 to 80 C,Diethylenetriamine pentaacetic acid dianhydride was obtained.

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  • 3
  • [ 23911-26-4 ]
  • [ 124-30-1 ]
  • [ 135546-68-8 ]
YieldReaction ConditionsOperation in experiment
90% In N,N-dimethyl-formamide at 50℃; 4 The DTPA bisanhydride is suspended in the DMF. The suspension is heated to 50° C. and dissolution takes place. The octadecylamine is added in a single portion. The reaction is maintained at 50° C. overnight. During the reaction, the amine is seen to slowly dissolve in the DMF, followed by precipitation of the desired product.10251] The reaction medium is cooled and then filtered through a sinter funnel. The precipitate is washed once with DMF and then thoroughly with methanol. 13.5 g of yellow-white powder are obtained with ayield of 90%. The mass spectrometry analysis is performed byinfusion of the sample in ES+. The product can be dissolvedin methanol or toluene by adding TFA.
49.9% In tetrahydrofuran for 48h; Heating;
45% In chloroform; N,N-dimethyl-formamide at 40℃; for 2h;
In chloroform; N,N-dimethyl-formamide at 40℃; for 2h; 9.i DTPABis(stearylamide) (DTPA-SA) is prepared by methods similar, to those previously reported by Jasanada et al. (Jasanada, F. et al. Indium-I l l labeling of low density lipoproteins with the DTPA- bis(stearylamide): evaluation as a potential radiopharmaceutical for tumor localization. Bioconjugate Chemistry. 1996 ]&n-Feb; 7(1):72-81); briefly stearylamine (2 mmol) in chloroform (40ml) is slowly added to DTPA (1.1 EPO mmol) in DMF (50 ml). After 2 hours of stirring at 40 0C the solution is cooled at 40C for 2 hours. The white precipitate is filtered, washed with acetone and dried overnight at 80°C. The precipitate will then be crystallized in boiling ethanol (800 ml). After 24 hours at room temperature, the small crystals is collected by filtration and washed with water (800 ml, 80 0C for 3 hours) and chloroform (800 ml, reflux for 3 hours) to eliminate unreacted DTPA and SA. The purity of the product is checked with TLC and MALDI- TOF mass spectrometry.

  • 4
  • [ 23911-26-4 ]
  • [ 19840-99-4 ]
  • [[2-(Bis-carboxymethyl-amino)-ethyl]-(2-{(2-hydroxy-acetyl)-[(4-methyl-2-oxo-1,2-dihydro-quinolin-7-ylcarbamoyl)-methyl]-amino}-ethyl)-amino]-acetic acid [ No CAS ]
  • 5
  • [ 23911-26-4 ]
  • [ 932-52-5 ]
  • {{2-[carboxymethyl-(2-{carboxymethyl-[(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-methyl]-amino}-ethyl)-amino]-ethyl}-[(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
  • 6
  • [ 5250-72-6 ]
  • [ 23911-26-4 ]
  • {{2-[carboxymethyl-(2-{carboxymethyl-[(2,3-dichloro-4,6-disulfamoyl-phenylcarbamoyl)-methyl]-amino}-ethyl)-amino]-ethyl}-[(2,3-dichloro-4,6-disulfamoyl-phenylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 20℃; for 4h;
With N,N-dimethyl-formamide at 20℃; for 4h;
  • 7
  • [ 23911-26-4 ]
  • [ 53297-68-0 ]
  • {{2-[carboxymethyl-(2-{carboxymethyl-[(2-chloro-4-sulfamoyl-phenylcarbamoyl)-methyl]-amino}-ethyl)-amino]-ethyl}-[(2-chloro-4-sulfamoyl-phenylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
  • 8
  • [ 23911-26-4 ]
  • [ 462-94-2 ]
  • [ 19840-99-4 ]
  • {{2-[(2-[(5-amino-pentylcarbamoyl)-methyl]-carboxymethyl-amino}-ethyl)-carboxymethyl-amino]-ethyl}-[(4-methyl-2-oxo-1,2-dihydro-quinolin-7-ylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
  • 9
  • [ 23911-26-4 ]
  • [ 51-06-9 ]
  • [ 923952-46-9 ]
  • 10
  • [ 23911-26-4 ]
  • [ 83392-10-3 ]
  • C48H89N9O16 [ No CAS ]
  • 11
  • [ 23911-26-4 ]
  • [ 19840-99-4 ]
  • DTPA-cs124 [ No CAS ]
  • 12
  • [ 23911-26-4 ]
  • [ 170572-38-0 ]
  • 6,9-bis(carboxymethyl)-3-(2-oxo-6,9,12,15,18,21,24-heptaoxa-3-azapentacosyl)-11-oxo-15,18,21,24,27,30,33-heptaoxa-3,6,9,12-tetraazatetratriacontanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;
  • 13
  • [ 23911-26-4 ]
  • [ 488-43-7 ]
  • [ 189941-88-6 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: diethylenetriaminepentaacetic dianhydride; 1-Amino-1-deoxy-D-glucitol In dimethyl sulfoxide at 40℃; for 4h; Stage #2: With potassium hydroxide In methanol; dimethyl sulfoxide 3.a Example 3.a) Preparation of 3,6,9-triaza-3,6,9-tricarboxymethylundecanoic acid bis-glucopyranosylamide a) Preparation of 3,6,9-triaza-3,6,9-tricarboxymethylundecanoic acid bis-glucopyranosylamide A solution of glucosamine (1.00 g; 0.00463 mol) in DMSO (10 ml) is charged into a 100-ml reaction flask and kept under stirring at 40 °C. A solution of diethylenetriaminopentaacetic acid bis-anhydride obtained as described in step a) of Example 1 (0.746 g; 0.00209 mol) in DMSO (5 ml) is slowly added thereto and the reaction mixture is stirred under nitrogen atmosphere for 4 hours.. methanolic KOH is added to bring the PH of the reaction mixture to 8 and the reaction product is then precipitated by addition of methanol followed by the addition of acetone.. The precipitate is washed several times with fresh acetone to remove DMSO still present and the product is then dried under vacuum.. Yield 64 %.
  • 14
  • [ 23911-26-4 ]
  • [ 111-95-5 ]
  • [ 185214-82-8 ]
YieldReaction ConditionsOperation in experiment
74% In DMF (N,N-dimethyl-formamide); at 80℃; for 24h; EXAMPLE 5 Synthesis of DTPA bis(di(2-methoxyethyl-amide)(3) 12.4 ml of bis(2-methoxyethyl)amine (0.084 mol), dissolved in 40 ml of anhydrous DMF, are added dropwise to 5_grams of DTPA anhydride (0.014 mol), dissolved in 80_ml of anhydrous DMF, under argon at 80 C. The reaction medium is kept stirred for 24 hours.After concentrating and addition of diethyl ether, the oily precipitate is separated from the solvents by settling.This residue is dissolved in the minimum amount of CHCl3 and reprecipitated from Et2O. After drying under vacuum, a hygroscopic foam (3) is obtained (6.43 g, yield of 74%), used without additional purification. 1H NMR (D2O+NaOD): 2.50 (t, 4H), 2.52 (t, 4H), 2.98 (s, 2H), 3.11 (s, 4H), 3.31 (s, 6H), 3.32 (s, 6H), 3.51 (s, 4H), 3.53-3.56 (m, 16H).13C NMR (D2O): 45.94, 47.03, 47.81, 49.75, 53.69, 56.29, 57.78, 67.16, 69.56, 69.69 (CH2); 58.63, 59.07 (OCH3); 166.9, 170.5, 175.7 (CO2H and CO). ES-MS: ES-: 622.1 ([M-H]-), ES+: 624.3 ([M+H]+), 646.2 ([M+Na]+).
  • 15
  • [ 23911-26-4 ]
  • [ 3119-15-1 ]
  • [ 913816-97-4 ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide; at 60℃; for 5.0h; Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60C for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.80~2.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243.
80% In N,N-dimethyl-formamide; at 60℃; for 5.0h; 10.0 g (25 mmol) of DTPA was dispersed in 20 ml of pyridine. 18 g (0.18 mol) of acetic anhydride was added to the dispersion, and a reaction was allowed to take place at 65 for 24 hrs with stirring. After the reaction was completed, the reaction mixture was filtered to recover generated material. The recovered compound was washed with acetic anhydride and diethyl ether several times, and dried under pressure for 24 hrs, thereby obtaining a DTPA anhydride at a yield of 78%. IR(cm-1) 2979, 1820, 1774, 1641. Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.802.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243.
  • 16
  • [ 23911-26-4 ]
  • [ 3119-15-1 ]
  • DTPA-bis(3-amido-2,4,6-triiodobenzoic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In N,N-dimethyl-formamide; at 60℃; for 5.0h; 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.13 g (2 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60C for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 75%. 1H NMR (D2O+NaOD, ppm) 2.34 m, 8H, CH2CH2), 2.78~2.86 (d, 10H, CH2CO), 7.92 (s, 2H, Ar-H).
75% In N,N-dimethyl-formamide; at 60℃; for 5.0h; 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.13 g (2 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 75%.
  • 17
  • [ 23911-26-4 ]
  • [ 138-37-4 ]
  • {{2-[carboxymethyl-(2-{carboxymethyl-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-ethyl)-amino]-ethyl}-[(4-sulfamoyl-benzylcarbamoyl)-methyl]-amino}-acetic acid [ No CAS ]
  • 19
  • [ 23911-26-4 ]
  • [ 998-07-2 ]
  • [ 217327-40-7 ]
YieldReaction ConditionsOperation in experiment
The synthesis of DTPA-PE is routinely performed by incubating PE with cyclic DTPA anhydride (cDTPAA), followed by column chromatography purification. Gd incorporation is then achieved by treating gadolinium chloride hexahydrate (Aldrich, Milwaukee, WI) with DTPA- PE and purified Gd-DTPA-PE complexes using column chromatography. A schematic representation of this synthesis is depicted in FIG. 2.
  • 20
  • [ 23911-26-4 ]
  • [ 29094-61-9 ]
  • [ 848488-95-9 ]
YieldReaction ConditionsOperation in experiment
61.7% <strong>[29094-61-9]Glipizide</strong> (445.5 mg, 1.0 mmol) was dissolved in DMSO (anhydrous, 10ML). Sodium amide (76.03mg, 2. 0 mmol) was then added. The reaction mixture was stirred at room temperature for 10 min. DTPA-dianhydride (357.32 mg, 1.0 mmol) was dissolved in DMSO (anhydrous, 10ML). Sodium amide (76.03 mg, 2.0 mmol) was then added. The reaction mixture was stirred at room temperature for 10 min. DTPA-dianhydride (357.32 mg, 1.0 mmol) dissolved in 5 ml DMSO (anhydrous) was added and the mixture was stirred for 4 hours. The mixture was added with water (10 mL), followed by 1N-sodium hydroxide solution (3 mL) and stirred for 2 hours. The solid was filtered and washed with water. This recovered starting material was 142.6 mg (32%) after drying under vacuum. The aqueous phase was dialyzed with membrane (MW CO < 500) for 2 days. DTPA-GLP (506.6 MG, ; 61.7% yield) as a white solid was gathered after lyophilization. The synthetic scheme is shown in Figure 8. Figures 9-17 SHOWED LH-, L3C-NMR spectrum and assignment and mass spectrometry of DTPA-<strong>[29094-61-9]glipizide</strong>.
  • 21
  • [ 23911-26-4 ]
  • [ 10238-21-8 ]
  • [ 848488-96-0 ]
YieldReaction ConditionsOperation in experiment
80% Glyburide (494.0 mg, 1. 0 mmol) was dissolved in DMSO (anhydrous, 5 ML). Sodium amide (195.0 mg, 5.0 mmol) was then added. The reaction mixture was stirred at room temperature for 10 MIN. DTPA-DIANHYDRIDE (357.32 mg, 1. 0 mmol) dissolved in 5 ml DMSO (anhydrous) was added and the mixture was stirred for 22 hours. The dark green colored mixture was added with water (10 ML), followed by IN-sodium hydroxide solution (5 mL) and stirred for 2 hours. The solid was filtered and washed with water. This recovered starting material was 88. 9 mg (18%) after drying under vacuum. The aqueous phase was dialyzed with membrane (MW CO < 500) for 2 days. DTPA-LB (695.5 mg, 80% yield) as a white solid was gathered after lyophilization. The synthetic scheme is shown in Figure 18. Figures 19-25 SHOWED LH-, 13C-NMR SPECTRUM and assignment of glyburide and DTPA-glyburide.
  • 22
  • [ 23911-26-4 ]
  • [ 1310446-26-4 ]
  • [ 19840-99-4 ]
  • [ 1174006-41-7 ]
  • 23
  • [ 23911-26-4 ]
  • [ 617-45-8 ]
  • DTPA-bis-amide-aspartic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 75℃; for 12h; Example 1-2Preparation of DTPA-bis-amide-aspartic acid (L2) of Formula 1To a stirred suspension of 0.71 g (2 mmol) of DTPA-bis-anhydride in 15 mL of N,N-dimethylformamide (DMF) was added 0.53 g (4 mmol) of aspartic acid. The mixture was stirred at 75 C. for 12 hours, and the solvent was completely removed under low pressure, and the residue was dissolved in 10 mL of methanol. The solution was passed through a short column of silica gel (60 mesh) with methanol. The eluate was precipitated in 250 mL of acetone, followed by filtration. The obtained white solid product was dried under vacuum at 65 C. for 10 hours. FIG. 1(b) is a schematic diagram of the synthetic method, and the result of Maldi-TOF mass spectrometry is shown in FIG. 4.
  • 24
  • [ 23911-26-4 ]
  • [ 7242-92-4 ]
  • DTPA-bis(2-norbornyl) [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% In chloroform at 20℃; Reflux;
  • 25
  • [ CAS Unavailable ]
  • [ 23911-26-4 ]
  • [ 109-85-3 ]
  • [ 131069-91-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methoxyethylamine With hydrogenchloride In water at 18 - 52℃; Stage #2: diethylenetriaminepentaacetic dianhydride With sodium hydroxide In water at 13 - 44.6℃; for 1.5 - 2.5h; Stage #3: gadolinium(III) oxide With hydrogenchloride more than 3 stages; 21; 22; 23 Gadolinium(III) complex of DTPA-bis(methoxyethylamide) (gadoversetamide) was synthesized from DTPA bis-anhydride and 2-MEA starting materials in aqueous solvent system without prior isolation and purification of versetamide.[0095] Water (160 mL) was added to a 3-neck round bottom flask equipped with an overhead stirrer, a temperature probe, and a pH probe. The water temperature was 18.6°C. 2-MEA (42.88 g) was added to the water, and the stirrer was set to stir the solution at 500 rpm. Upon addition of the 2- MEA, the solution temperature was 19.4°C, and the solution pH was 12.14. Concentrated HCl solution was added to lower the pH to 8.02, and the solution was allowed to cool to about 18°C. DTPA bis- anhydride (100.86 g) was added to a powder feeder set at a rate to add the powder to the reaction solution over the course of 1.5 to 2 hours. The addition of the DTPA bis-anhydride lowered the solution pH to 2.19 and raised the solution temperature to 30.10C. IO N NaOH solution was used to raise the pH back to about 8 and maintain the solution pH at about 8 throughout the reaction. Additionally, an ice bath was used to maintain the solution temperature between about 18°C and about 200C. Upon addition of all of the DTPA bis-anhydride, an aliquot was taken and analyzed by liquid chromatography .[0096] The solution containing versetamide was divided into two solutions of roughly equal volume. The first versetamide solution was added to a round bottom flask equipped with an overhead stirrer, a temperature probe, and a reflux condenser. This solution had a volume of about 215 mL and a pH of 8.35. The solution pH was lowered to 2.00 with concentrated HCI solution. Gadolinium oxide, Gd2O3, (24.12 g) was added, and the solution was heated to 1000C and refluxed at that temperature for over 16 hours; Gadolinium(III) complex of DTPA-bis(methoxyethylamide) (gadoversetamide) was synthesized from DTPA bis-anhydride and 2-MEA starting materials in aqueous solvent system without prior isolation and purification of versetamide.[0101] Water (100 mL) was added to a 3-neck round bottom flask equipped with an overhead stirrer, a temperature probe, and a pH probe. 2-MEA (42.88 g) was added to the flask, and the stirrer was set to stir the solution at about 54 rpm. Addition of the 2-MEA raised the solution temperature from 21.7°C to 36.8°C, and the solution pH increased to 13.77. Concentrated HCl solution was added to lower the pH to 7.99. Adding the HCl raised the solution temperature to 47.5°C, so the solution was cooled to 32.3°C using an ice bath. DTPA bis-anhydride (103.24 g) was added to a powder feeder set at a rate to feed the powder to the reaction mixture over about 2.5 hours. The addition of the DTPA bis- anhydride lowered the solution pH and raised the solution temperature. 10 N NaOH solution was used to maintain the solution pH at about 8 throughout the reaction. Additionally, an ice bath was used to maintain the solution temperature between about 18°C and about 26°C. Aliquots were taken periodically and analyzed by liquid chromatography to monitor the formation of versetamide. Upon completion of the reaction, the solution was filtered through a 0.45 μm filter and returned to the reaction flask.[0102] The solution pH was lowered to 3.75 using concentrated HCl solution. The flask was placed on a heating mantle, and the solution was heated to about 800C, which took about 10 minutes. Gadolinium oxide, Gd2O3 (48.19 g) was added to the reaction mixture, and the heated solution was refluxed for about 2 hours. Aliquots were taken periodically and analyzed by liquid chromatography to monitor the formation of gadoversetamide. The pH was monitored during the reaction and maintained at about 4 using concentrated HCl solution. HPLC analysis indicated the gadoversetamide product was 96.69% pure.Example 23. Total Synthesis of Gadoversetamide in Aqueous Solvent System[0103] Gadolinium(III) complex of DTPA-bis(methoxyethylamide) (gadoversetamide) was synthesized from DTPA bis-anhydride and 2-MEA starting materials in aqueous solvent system without prior isolation and purification of versetamide.[0104] Water (100 mL) was added to a 3-neck round bottom flask equipped with an overhead stirrer, a temperature probe, and a pH probe. 2-MEA (42.88 g) was added to the water, and the stirrer was set to stir the solution at about 54 rpm. Addition of the 2-MEA raised the solution temperature from 19.10C to 35.8°C, and the solution pH increased to 13.46. Concentrated HCl solution was added to lower the pH to 7.98. Adding the HCl raised the solution temperature to about 52°C, so the solution was cooled to 35.3°C using an ice bath. DTPA bis-anhydride (102.33 g) was added to a powder feeder set at a rate to feed the powder to the reaction mixture over about 2 hours. The addition of the DTPA bis-anhydride lowered the solution pH to 3.47 and raised the solution temperature to 44.60C. IO N NaOH solution was used to maintain the solution pH at about 8 throughout the reaction. Additionally, an ice bath was used to maintain the solution temperature between about 130C and about 26°C. Aliquots were taken periodically and analyzed by liquid chromatography to monitor the formation of versetamide. Upon completion of the reaction, the solution was filtered through a 0.45 μm filter and returned to the reaction flask.[0105] The solution pH was lowered to 3.99 using concentrated HCl solution. The flask was placed on a heating mantle, and the solution was heated to about 800C, which took about 10 minutes. Gadolinium oxide, Gd2C^, (48.22 g) was added to the reaction flask, and the heated solution was refluxed for about 2 hours. Aliquots were taken periodically and analyzed by liquid chromatography to monitor the formation of gadoversetamide. The pH was monitored during the reaction and maintained at about 4 using concentrated HCl solution. HPLC analysis indicated the gadoversetamide product was 98.1% pure.
  • 26
  • [ 23911-26-4 ]
  • [ CAS Unavailable ]
  • [ 109-85-3 ]
  • [ 131069-91-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: diethylenetriaminepentaacetic dianhydride; 2-methoxyethylamine In water at 10℃; for 1.5 - 2h; Stage #2: gadolinium(III) nitrate In water for 0.833333h; Stage #3: With sodium hydroxide In water 20 Gadolinium(III) complex of DTPA-bis(methoxyethylamide) (gadoversetamide) was synthesized from DTPA bis-anhydride and 2-MEA starting materials in aqueous solvent system without prior isolation and purification of versetamide.[0092] To prepare versetamide, 2-methoxyethylamine (85.1 g 2-MEA, BASF) was added to water (700 mL) contained in a reaction flask. The pH of the solution after adding the 2-MEA was about 13. The solution was cooled to 100C using an ice bath. DTPA bis-anhydride (200 g) was added to the reaction flask incrementally over the course of 1.5 to 2 hours to maintain the solution temperature at about 100C. Because the aqueous solution was non-buffered, the addition of the DTPA bis- anhydride lowered the solution pH to about 3.2. Aliquots of the reaction composition were taken periodically and analyzed by HPLC (Altima Cl 8 column, 4.6 x 250 mm, 10 μm particles, 1 mL/min flow rate using 93:7 v:v pH 2.5 phosphate buffeϖacetonitrile buffer solution) to monitor the formation of versetamide.[0093] Upon completion of the versetamide reaction, gadolinium nitrate, Gd(NO3)3 '6H2O solution (28.85g in 250 mL water) was added to the reaction flask containing the versetamide. The pH decreased to about 0.7 upon addition of the gadolinium nitrate. After 50 minutes, the pH of the solution was raised to about 7.7 using IO N NaOH solution. Water was removed by rotary evaporation, leaving solid gado versetamide product and nitrate salts. The product was purified by redissolving the solids in water and reverse osmosis.
Stage #1: 2-methoxyethylamine With hydrogenchloride In water at 18 - 19.4℃; Stage #2: diethylenetriaminepentaacetic dianhydride With sodium hydroxide In water at 18 - 30.1℃; for 1.5 - 2h; Stage #3: gadolinium(III) nitrate With hydrogenchloride; sodium hydroxide In water for 1h; 21 Gadolinium(III) complex of DTPA-bis(methoxyethylamide) (gadoversetamide) was synthesized from DTPA bis-anhydride and 2-MEA starting materials in aqueous solvent system without prior isolation and purification of versetamide.[0095] Water (160 mL) was added to a 3-neck round bottom flask equipped with an overhead stirrer, a temperature probe, and a pH probe. The water temperature was 18.6°C. 2-MEA (42.88 g) was added to the water, and the stirrer was set to stir the solution at 500 rpm. Upon addition of the 2- MEA, the solution temperature was 19.4°C, and the solution pH was 12.14. Concentrated HCl solution was added to lower the pH to 8.02, and the solution was allowed to cool to about 18°C. DTPA bis- anhydride (100.86 g) was added to a powder feeder set at a rate to add the powder to the reaction solution over the course of 1.5 to 2 hours. The addition of the DTPA bis-anhydride lowered the solution pH to 2.19 and raised the solution temperature to 30.10C. IO N NaOH solution was used to raise the pH back to about 8 and maintain the solution pH at about 8 throughout the reaction. Additionally, an ice bath was used to maintain the solution temperature between about 18°C and about 200C. Upon addition of all of the DTPA bis-anhydride, an aliquot was taken and analyzed by liquid chromatography .[0096] The solution containing versetamide was divided into two solutions of roughly equal volume. The first versetamide solution was added to a round bottom flask equipped with an overhead stirrer, a temperature probe, and a reflux condenser. This solution had a volume of about 215 mL and a pH of 8.35. The solution pH was lowered to 2.00 with concentrated HCI solution. Gadolinium oxide, Gd2O3, (24.12 g) was added, and the solution was heated to 1000C and refluxed at that temperature for over 16 hours.[0097] The second versetamide solution was added to a round bottom flask equipped with an overhead stirrer, a temperature probe, and a pH probe. This solution had a volume of about 220 mL and a pH of 8.45. Gadolinium nitrate hexahydrate, Gd(NO3)3 -6H2O, (15.99 g) was added with water (5 mL), which lowered the solution pH slightly to 7.03. The pH was lowered to about 2.0 using concentrated HCl and 10 N NaOH solutions. The solution was stirred for 1 hour and upon completion of the reaction, the pH of the solution was raised to about 7 to 8 using I O N NaOH solution.
  • 27
  • [ 23911-26-4 ]
  • [ 113411-20-4 ]
  • [ 1258784-05-2 ]
YieldReaction ConditionsOperation in experiment
With water at 20℃; 7 Compound 7{Carboxymethyl-II^carboxymethyl-fl-lcarboxymethyl-dKS-sulfamoyl-ll^^lthiadiazol-l- ylcarbamoyl)-methylj-carbamoyl}-methyl)-ainino]-ethyl}-amino)-ethyl]-amino}-acetic acid[00343] DTPA anhydride (O.Ommol) and 2-amino-N-(5-sulfamoyl-[ 1 ,3,4]thiadiazol-2-yl)- acetamide (Intermediate 7, 0.15mmol) were weighted and dissolved in 1.OmL water, and then a traceable amount of sodium carbonate was used to adjust pH value to 9. The mixture was stirring for 2-4 hour under room temperature. After the reaction solution was diluted with 3.0 mL acidic water and purified with LC- MS system (all are same with analytical LC-MS system except that flow rate for purification is 20.0 mL/min and column is 19x l50mm, Xbridge PreCis OBD) to afford pure title compound, which were characterized with LC-MS system for its purity and molecular weight after lyophilization.
  • 28
  • [ 23911-26-4 ]
  • [ 52-66-4 ]
  • [ 1240360-15-9 ]
  • 29
  • [ 23911-26-4 ]
  • [ 93324-65-3 ]
  • 1,4,7-tris(methylenecarboxy)-1,7-bis(N-1-pyrenylmethylacetamide)-1,4,7-triazaheptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine In N,N-dimethyl-formamide at 20℃;
  • 30
  • [ 23911-26-4 ]
  • [ 62-31-7 ]
  • [ 147666-97-5 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine; In N,N-dimethyl-formamide; at 75℃; for 24h; To a solution of 3-hydroxytyramine hydrochloride (0.99 g, 5.2 mmol) in DMF (50 mL), 0.74 mL of triethylamine (11.3 mmol) was added followed by 0.85 g of DTPA dianhydride (5.6 mmol). After 24 h under stirring at 75 C, the mixture was concentrated and the precipitate formed was filtered off. The filtrate was evaporated and the residue was dissolved in ethanol. Addition of chloroform led to a precipitate and compound 2a (0.98 g, 62%) was obtained as white powder after filtration.1H NMR (D2O, 300 MHz, 25 C) delta=6.76 (d, J=8.1 Hz, 2H, Ar-H), 6.70 (d, J=1.7 Hz, 2H, Ar-H), 6.57 (dd, J=1.7 and 7.8 Hz, 2H, Ar-H), 3.70 (s, 4H, NCH2CO2H), 3.58 (s, 4H, NCH2C(O)NH-), 3.52 (s, 2H, NCH2CO2H), 3.38 (t, J=6.4 Hz, 4H, NCH2CH2N), 3.11 (t, J=6.7 Hz, 4H, NHCH2CH2Ar), 2.97 (t, J=6.7 Hz, 4H, NHCH2CH2Ar), 2.61 (t, J=6.4 Hz, 4H, NCH2CH2N). 13C NMR (D2O, 75 MHz, 25 C) delta=172.4 (CO), 171.9 (CO), 168.3 (CO), 144.3 (ArC), 142.8 (ArC), 132.2 (ArC), 121.5 (ArCH), 117.0 (ArCH), 116.5 (ArCH), 56.9 (CH2), 56.5 (CH2), 51.8 (CH2), 51.3 (CH2), 40.9 (CH2), 34.0 (CH2). ES-MS found: 664.0 ([M+H]+).
  • 31
  • [ 23911-26-4 ]
  • [ 13080-85-8 ]
  • [ 1364601-70-6 ]
  • 32
  • [ 23911-26-4 ]
  • [ 2486-80-8 ]
  • [ 1391921-94-0 ]
YieldReaction ConditionsOperation in experiment
27% With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;
  • 33
  • [ 23911-26-4 ]
  • [ 5818-06-4 ]
  • C28H35N7O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.8% With pyridine In water at 20℃; for 24h;
  • 34
  • [ 23911-26-4 ]
  • [ 118-31-0 ]
  • [ 138886-03-0 ]
YieldReaction ConditionsOperation in experiment
90% In N,N-dimethyl-formamide at 20℃; for 24h; 1,4,7-Tris(methylenecarboxy)-1,7-bis(N-1-naphthylacetamide)-1,4,7-triazaheptane:compound 4 (dtpa1nap)H3 General procedure: (Dtpa1nap)H3 was synthesised by a method similar tothat reported for DTPA-bis(ethylamide) (DTPA: diethylenetriaminepentaacetate)(28): solid DTPA dianhydride(0.250 g, 0.70 mmol) was added to 1-aminonaphtalene(0.250 g, 1.75 mmol) dissolved in DMF (15 mL) withstirring at room temperature, and the reaction wasallowed to continue for 24 h. Any solid in the resultingreaction mixture was removed by filtration. The filtratewas concentrated to a viscous liquid. Addition of cooledacetone (50 mL, 4°C) gave a pale pink solid, which wascollected by filtration, washed with a small volume ofcooled acetone (4°C) and dried in vacuum for 4 h. Theresulting solid was suspended in water (100 mL) anddissolved by adding a minimum amount of solidNa2CO3. When the solution, after being filtered, wasacidified to pH 2.6 with 0.1 M HCl, a creamy precipitatewas formed, which was collected by filtration, washedwith copious amounts of water and dried in vacuum for6 h (154 mg). The solid was dissolved again in waterwith a minimum amount of Na2CO3, and any insolublesubstance was removed by filtration. Acidification ofthe resulting clear solution to pH 1.8 with HCl0.2 M gave compound 4 in the acid form as a lightbrown solid, which was separated by filtration, washedthoroughly with water and dried in vacuum (0.128 g,13%). 49
87% With L-ascorbic acid sodium salt In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
  • 36
  • [ 23911-26-4 ]
  • [ 104-42-7 ]
  • C50H78N5O8(3-)*Eu(3+) [ No CAS ]
  • 37
  • [ 23911-26-4 ]
  • [ 7089-68-1 ]
  • [ 24424-99-5 ]
  • [ 14235-81-5 ]
  • [ 1609542-53-1 ]
  • C39H43N7O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
[2-[(4?-Aminophenylen)ethynylen]-l ,1 0-phenanthrolin-5/6-yl]amine 5 (1 eq.), DTPAdianhydride and triethylamine (5 eq.) were stirred in DMF under argon for 2 h at 80°C. The solvents were removed under reduced pressure. The residue was purified by RP-HPLC(water/MeCN).A potential problem regards the coupling of the antenna (compound 5) with the chelator (DTPA-anhydride) as the used DTPA- anhydride has two activated acid groups, but only the monosubstituted product is desired. The formation of a disubstituted product was reduced by applying the suitable excess of DTPA as described above and by a reaction design thatkeeps the concentration of compound 5 as small as possible.
Example 1: Syntheis of the amino-reactive phosphorescent dye of the invention Nitration of <strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> 150 ml concentrated sulphuric acid was placed in a 500 ml three-necked flask and <strong>[7089-68-1]2-Chloro-1,10-phenanthroline</strong> 1 (CAS-Nr. 7089-68-1)(30g) was added while cooled with ice and stirred. The solution was heated in an oil bath to 180 °C. At 80 °C, the solution boiled and a strong smoke emission could be observed. At 160 °C, nitric acid (65 percent, 80 ml) was added dropwise while maintaining a temperature of 170 °C. The bath temperature was increased to 215 °C, and the adding was performed in such a way that the temperature was below or equal to 160 °C. After complete addition of the nitric acid, the solution was heated under reflux for 1 h to 165 to 170 °C. Following this, the reaction mixture was cooled in a ice bath, added to approximately 1 kg ice and diluted with 1 l water. A sodium hydroxide solution (50 percent w/v) was added dropwise until the pH value of the reaction mixture was in a neutral/weak alkaline range. This was accompanied by formation of a slightly yellow precipitate. The precipitate was separated and washed with water. The crude product of the reaction was dried over night at 110 °C, extracted with chloroform via Soxleth extraction and reduced to a dry powder in rotary evaporator. Reduction of 2-chloro-5/6-nitro-1,10-phenanthroline 2-Chloro-5/6-nitro-1,10-phenanthroline 2 (1 eq.) was dissolved in methanol and hydrogenated under stirring in the presence of the catalyst (palladium/coal 10percent, 10molpercent) in a hydrogenation plant until no further hydrogen consumption could be observed. The catalyst was filtered off and the filtrate was reduced to dryness under reduced pressure (complete conversion). Introduction of a Boc group to 5/6-amino-<strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> Alternatively, the amine group of <strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> 3 may be protected with a Boc group. To do this, 5/6-amino-<strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> (1 eq.) was dissolved in dry DMF and triethylamine (5 eq.). Then, DMAP (1.1 eq.) and di-t-butyldicarbonate (2 eq.) were added The solution was stirred at room temperature for 20 h. Then, water was added and the aqueous phase was extracted three times with diethylether. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product was purified with silica gel (CH2Cl2). (63percent yield). Coupling of the Boc-protected 2-chloro-5/6-amino-1,10-phenanthroline and 4-ethinylaniline Triphenylphosphine (30 molpercent), [Pd(PPh3)2]Cl2 (3molpercent), the protected 2-chloro-5/6-amino-1,10-phenanthroline 4 (1 eq.) and copper(I)iodide (2molpercent) were placed in a three-necked flask and suspended in 30 ml methanol. The 4-ethinylaniline (1.2 eq.) was added dissolved in 20 ml methanol. The reaction mixture was refluxed for 10 h. The mixture was extracted three times with dichloromethan, respectively. The combined organic phases were washed with water and brine before being concentrated to dryness. Purification by flash-chromatography yielded compound 5 as a brown solid. Coupling of the 19 Boc-protected [2-[(4'-aminophenylen)ethynylen]-1,10-phenanthrolin-5/6-yl]amine and DTPA-anhydride [2-[(4'-Aminophenylen)ethynylen]-1,10-phenanthrolin-5/6-yl]amine 5 (1 eq.), DTPA-dianhydride and triethylamine (5 eq.) were stirred in DMF under argon for 2 h at 80°C. The sovents were removed under reduced pressure. The residue was purified by RP-HPLC (water/MeCN).
  • 38
  • [ 23911-26-4 ]
  • [ 645-35-2 ]
  • [ 1042129-71-4 ]
YieldReaction ConditionsOperation in experiment
81% To a suspension of <strong>[645-35-2]histidine hydrochloride</strong> (1.5 g, 8.0 mmol) in CH2Cl2 (15 mL) was added triethylamine (5 mL). The mixture was stirred at room temperature for 1 h, after which DTPA-bis(anhydride) (1.4 g, 4.0 mmol) was in portions. The solution was further stirred for 6 h. The solvent was removed, and the residue taken up in methanol (5 mL) to be passed through a short silica gel column to remove any solid impurities. The solution was then applied to column chromatography with methanol as an eluent. The product was obtained as an off-white solid after removal of the solvent under vacumn. Yield: 0.87 g (81%).
  • 39
  • [ 23911-26-4 ]
  • [ 121268-17-5 ]
  • C22H43N5O22P4(2-)*2Na(1+) [ No CAS ]
  • 40
  • [ 67-43-6 ]
  • [ 108-24-7 ]
  • [ 23911-26-4 ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; at 65℃; for 24h; It must be pointed out that the diethylenetriamine pentaacetic aciddianhydride (dtpaa) is demand for the start of all experiments and itssynthesis procedure is described in Scheme 1. <strong>[67-43-6]Diethylenetriaminepentaacetic acid</strong> (dtpa) (7.80 g, 0.02 mmol) was dissolved in acetic anhydride(8.00 mL, 0.08 mmol) and pyridine (10.00 mL, 0.12 mmol) asacid-binding agent under anhydrous condition. The mixed solutionwas stirred for one day under heat-refluxing at 65 C. Afterwards, thereaction mixture was cooled down to room temperature, and the solventwas removed by reduced pressure filter. The residue washedtwice by acetic anhydride and anhydrous diethyl ether. Finally, the residuewas dried to give 6.50 g white powder under vacuum (52 kpa) at80 C with yield of 83%. FT-IR (KBr, cm-1): 1642.41, 1772.10, 1821.08,2341.42, 2820.47 and 2979.80. 1H NMR (500 MHz, DMSO): d = 2.593(t, 4H), 2.748 (t, 4H), 3.300 (s, 2H), 3.705 (s, 8H) and 11.013 (s, 1H).
With pyridine; at 65℃; for 24h; Weigh dtpa 7.8100g (0.02mmol), acetic anhydride 16.0 mL (0.08 mmol), 10.0 mL (0.12 mmol) of pyridine was placed in a three-necked round bottom flask. Mix well and stir at 65 C for 24 h. Cool to room temperature and filter the reaction mixture. Wash twice with a small amount of acetic anhydride and anhydrous ether. The mixture was suction filtered with a vacuum pump, and the resultant was vacuum dried in a vacuum oven at 80 C. That is dtpaa.
  • 41
  • [ 23911-26-4 ]
  • [ 136-64-1 ]
  • C22H31N7O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.68 g In N,N-dimethyl-formamide; Compound 3: To a solution of DTPA-bisanhydride (3.57 g, 10 mmole) and triethylamine (5 ml) in 40 ml of dimethylformamide (DMF) was slowly added 0.18g of water (10 mmole) in 10 ml of dry DMF over a period of 2 hours. Compound 2 (10 mmol) was added and the reaction mixture was stirred overnight. After evaporation to dryness, the residue was evaporated to dryness. The resulting white powder was dissolved in a mixture of acetonitrile/H20 (1 : 1 , v/v) and purified by preparative RP-HPLC. Yield: 0.68g of white solid (1 .1 mmol; 1 1 %).
  • 42
  • [ 23911-26-4 ]
  • [ 136-64-1 ]
  • RF1404 [ No CAS ]
  • 43
  • [ 23911-26-4 ]
  • [ 73-40-5 ]
  • C24H29N13O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 24h; Dtpa-bis(guanine) ligand was synthesized by the aminolysis reactionbetween dtpaa and guanine and the synthesis procedure is shownin Scheme 1. Dtpaa (1.96 g, 55 mmol) was dissolved in DMF (50 mL)and Trithylamine as base under anhydrous condition. Subsequently, theguanine was added to the mixed solution slowly. The mixed solutionwas stirred 24 h under heat-refluxing at 100 C. The mixture was thencooled downto roomtemperature. After the solventwas removed by vacuumfilter, the white solid was obtained. The white solid was evaporatedto dryness under vacuum(52 kpa) at 50 C to give 2.30 g white powderysolid with yield of 92%. FT-IR (KBr, cm-1): 1668, 1710, 2691, 2854, 2908,3119 and 3321. 1H NMR (500 MHz, DMSO): d=2.010 (m, 2H), 2.717 (s,2H), 2.807 (d, 2H), 2.460 (t, 8H), 3.254 (s, 4H), 3.301 (s, 6H), 7.503 (d, 2H),7.973 (s, 2H) 8.010 (s, 2H) and 11.012 (s, 3H).
  • 44
  • [ 23911-26-4 ]
  • [ 100343-98-4 ]
  • C42H53N9O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide at 100℃; for 6h; 1.b BAll of the yellow solid obtained in step a was dissolved in 10 ml of DMF solution,Adding 0.5 times the molar amount of DTPA,Oil bath heated to reflux at 100 degrees for six hours, distillation of DMF under reduced pressure,A yellow solid was obtained in 80% yield,
  • 45
  • [ 23911-26-4 ]
  • [ 2243-61-0 ]
  • 2,12,25,35-tetraoxo-4,7,10,27,30,33-hexakis(carboxymethyl)-1,4,7,10,13,24,27,30,33,36-decaaza-[13.13](1,4)naphthalenophane [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.6% In N,N-dimethyl-formamide Syntheses of (bis-dtpa14nap)H6 A dimethylformamide (DMF) solution (60 mL) containing0.225 g (1.42 mmol) of 1,4-diaminonaphthalene(Aldrich) was added dropwise, through a dropping funnel,to 0.530 g (1.48 mmol) of DTPA dianhydride in300 mL of DMF with vigorous agitation over a periodof 4 h. After the resulting reaction mixture was left tostand overnight, any solid formed was removed by filtration,and the filtrate was concentrated to a viscous liquid.Addition of acetone (125 mL) gave an orange solid,which was separated by filtration, washed with acetoneand dried in vacuum. The crude product was dissolvedin water by adding a minimum quantity of solid Li2CO3,and the remaining carbonate was removed by filtration. Acidification of the solution to pH 4 with dilute HCl precipitatedthe 2+2 reaction product. After the treatmentof the solid with Li2CO3and HCl was repeated, the solutionwas acidified to pH 2 with 0.1 M HCl, and the purecompound was obtained in the acid form. The productwas washed thoroughly with water and dried in vacuum.Yield (0.041 g, 5.6%). M.p. 253-254 °C. Anal. Calcd. forC48H58N10O16·6H2O: C, 50.61; H, 6.19; N, 12.30. Found:C, 50.47; H, 6.24; N, 12.6. 1H NMR (D2O, 400 MHz,pD = 11.0) δ = 3.01 (br, 8H, Hb1in Scheme 1), 3.04 (br,8H, Hb2),3.34 (s, 4H, Ha2),3.44 (s, 8H, Ha1),3.56 (s,8H, Hc),7.11 (dd, J = 6.2, 3.1 Hz, 4H, H6),7.39 (s, 4H,H2),7.46 (dd, 4H, J = 6.4, 2.8 Hz, H5).13C NMR (D2O,100 MHz, pD = 10.97) δ = 52.4 (Cb1), 52.6 (Cb2), 57.4(Ca2), 58.7 (Ca1), 58.9 (Cc), 121.9 (C1,4), 122.4 (C5,8),126.5 (C2,3), 128.6 (C6,7), 130.4 (C9,10), 164.9 (Camide),174.7 (Ca1-COOH), 179.4 (Ca2-COOH). HR MS ESIm/z (%) = 1029.395 (100) [M-H]- C48H57N10O16(calcd.m/z = 1029.394).
  • 46
  • [ 23911-26-4 ]
  • [ 2016-42-4 ]
  • [(2-{carboxymethyl-[2-(carboxymethyl-tetradecylcarbamoylmethyl-amino)-ethyl]-amino}-ethyl)-tetradecylcarbamoylmethyl-amino]-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.9% In chloroform; N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere; Synthesis of DTPA-BA (3a-c) General procedure: Under a N2 atmosphere, 2 (0.50 g, 1.40 mmol) in anhydrousdimethyl formamide (DMF) was heated to 85 C.After the solid was entirely dissolved, the system temperaturewas cooled to 40°C and then dodecanamine (0.57 g,3.08 mmol) dissolved in trichloromethane was added to thesolution dropwise. The mixture was stirred for 2 h. Aftercooling and filtering, the residue was dissolved in 1 MNaOH, and then filtered again. The filtrate was adjusted topH 2-3 by adding 1 M HCl, filtered, and then the residuewas dried in vacuo overnight. The solid was recrystallizedfrom anhydrous EtOH and then dried in vacuo overnight.3b was recrystallized from a mixture of MeOH and chloroform,and 3c from n-butylalcohol.
  • 47
  • [ 23911-26-4 ]
  • [ 1162336-72-2 ]
  • C64H123N23O20 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h;
  • 48
  • [ 23911-26-4 ]
  • [ 71-30-7 ]
  • [ 73-24-5 ]
  • C22H29N9O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1. 135635g (5.5mmol) of diethylenetriamine pentaacetic acid dianhydride (dtpaa), 2.334mL of triethylamine (16.5mmol), anhydrous DMF (50mL), <strong>[73-24-5]adenine</strong> (A) 0.7432g (5.5mmol), In a three-necked round bottom flask. Stir at a constant temperature of 100 C, and condense and reflux for 24 h. Further, 0.6105 g (5.5 mmol) of cytosine was added to the above reaction solution, and the mixture was rapidly stirred at a constant temperature of 100 C, and condensed and refluxed for 24 hours. After completion of the reaction, the mixture was allowed to stand. After cooling to room temperature, the solvent was evaporated to give a white solid material, which was filtered, filtered, and then washed three times with acetonitrile and anhydrous diethyl ether (3×10 mL). After drying at 50 C, <strong>[73-24-5]adenine</strong>-diethylenetriamine pentaacetic acid-cytosine (dtpa-AC) was obtained.
  • 49
  • [ 23911-26-4 ]
  • [ 73-24-5 ]
  • C24H29N13O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 24h; Take diethylene triamine pentaacetic acid dianhydride (dtpaa) 1.9635g (5.5mmol),2.334 mL of triethylamine (16.5 mmol),Anhydrous DMF (50 mL),Adenine (A) 1.4864g (11mmol),In a three-necked round bottom flask.Stir at a constant temperature of 100 C, and condense and reflux for 24 h.After completion of the reaction, the mixture was allowed to stand. After cooling to room temperature, the solvent was evaporated to give a white solid material, which was filtered, filtered, and then washed three times with acetonitrile and anhydrous diethyl ether (3×10 mL).Drying at 50 C gives diethylene triamine pentaacetic acid - bis (<strong>[73-24-5]adenine</strong>) (dtpa-2A).
  • 50
  • [ 23911-26-4 ]
  • [ 2018-90-8 ]
  • 1,4,7-tris(methylenecarboxy)-1,7-bis(N-2-naphthylmethylacetamide)-1,4,7-triazaheptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In N,N-dimethyl-formamide at 20℃; for 24h; 1,4,7-Tris(methylenecarboxy)-1,7-bis(N-1-naphthylacetamide)-1,4,7-triazaheptane:compound 4 (dtpa1nap)H3 General procedure: (Dtpa1nap)H3 was synthesised by a method similar tothat reported for DTPA-bis(ethylamide) (DTPA: diethylenetriaminepentaacetate)(28): solid DTPA dianhydride(0.250 g, 0.70 mmol) was added to 1-aminonaphtalene(0.250 g, 1.75 mmol) dissolved in DMF (15 mL) withstirring at room temperature, and the reaction wasallowed to continue for 24 h. Any solid in the resultingreaction mixture was removed by filtration. The filtratewas concentrated to a viscous liquid. Addition of cooledacetone (50 mL, 4°C) gave a pale pink solid, which wascollected by filtration, washed with a small volume ofcooled acetone (4°C) and dried in vacuum for 4 h. Theresulting solid was suspended in water (100 mL) anddissolved by adding a minimum amount of solidNa2CO3. When the solution, after being filtered, wasacidified to pH 2.6 with 0.1 M HCl, a creamy precipitatewas formed, which was collected by filtration, washedwith copious amounts of water and dried in vacuum for6 h (154 mg). The solid was dissolved again in waterwith a minimum amount of Na2CO3, and any insolublesubstance was removed by filtration. Acidification ofthe resulting clear solution to pH 1.8 with HCl0.2 M gave compound 4 in the acid form as a lightbrown solid, which was separated by filtration, washedthoroughly with water and dried in vacuum (0.128 g,13%). 49
  • 51
  • [ 23911-26-4 ]
  • [ 2321-07-5 ]
  • C34H33N3O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 100℃; for 24h; 1.2 2. Preparation of dtpa-bis (fluorescein) with diethylenetriaminepentaacetic acid 1.9610 g of dtpaa (5.5 mmol) and triethylamine 8.0 mL (16.5 mmol) were taken. Anhydrous DMF (50 mL), fluorescein 1.6515 g (11 mmol), mix in a three-neck round bottom flask. Heated at a constant temperature of 100 ° C, stir for 24h quickly. After the reaction is completed, it is allowed to stand, and after cooling to room temperature, obtained a pale yellow solid substance, filtered, dried in vacuo at 50°C, that is dtpa-bis (fluorescein).
  • 52
  • [ 23911-26-4 ]
  • [ 1639876-58-6 ]
  • [ 76-05-1 ]
  • [ 2410051-51-1 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: diethylenetriaminepentaacetic dianhydride; 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butan-1-aminium trifluoroacetate In N,N-dimethyl-formamide for 5h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile 2 General procedure for the synthesis of compounds lOb-lOd General procedure: To a suspension of DTPA-dianhydride 9 (1 eq., 560 pmol, 200 mg) in anhydrous DMF (3 mL) in a 15 mL Falcon tube the linker trifluoroacetate 5b-5d (0.6 eq.) in anhydrous DMF (1 mL) was added in three portions over the course of 2 h (333 pL/h), the suspension was vortexed for a few seconds and the reaction was left stirring for 3h. Water (4 mL) was added to the suspension. The obtained solution was directly injected into a reversed-phase C18 cartridge and purified with flash chromatography. The purification was carried out using a step gradient, from 100% water (0.1% TFA) to 100% acetonitrile (0.1% TFA) over 10 column volumes. Fractions containing the product were combined and lyophilized to achieve the target compound as a fluffy white solid. (0645) Yield and characterization data for Ob-lOd (0646) (0647) [0289] 2-({2-[bis(carboxymethyl)amino]ethyl}({2-[(carboxymethyl)([4-(2,5-dioxo-2,5- dihydro-lH-pyrrol-l-yl)butyl]carbamoyl}methyl)amino]ethyl})amino)acetic acid 10b was prepared as described above. Yield: 44 mg (35% yield referring to the linker) (calculated as TFA salt. TFA content: 1.83 ± 0.23 mol. Eq.), HPLC (method 2, 220 nm) 98%. LRMS-ESI (m/z) calcd. for C22H33N5O11 [M+H]+: 544.53. Found: 544.27. NMR (400 MHz, D2O) d 6.82 (s, 2H), 4.11 (s, 4H), 4.04 (s, 2H), 4.03 (s, 2H), 3.72 (s, 2H), 3.54-3.45 (m, 6H), 3.27-3.20 (m, 6H), 1.62-1.46 (m, 4H); 13C NMR (101 MHz, D2O, as a TFA salt, the signals of TFA were not included) d 173.30, 172.91, 169.91, 166.51, 134.28, 56.27, 55.60, 55.54, 53.77, 52.56, 50.03, 49.93, 38.90, 37.08, 25.43, 24.96. (0648) [0290] 2-[2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)ethyl]([5-(2,5-dioxo- 2,5-dihydro-lH-pyrrol-l-yl)pentyl]carbamoyl}methyl)amino}acetic acid 10c was prepared as described above. Yield: 87 mg (36% yield referring to the linker) (calculated as TFA salt. TFA content: 1.46 ± 0.25 mol. Eq.), HPLC (method 2, 220 nm) 98%. LRMS-ESI m/z) calcd. for C23H35N5O11 [M+H]+: 558.56. Found: 558.26. NMR (400 MHz, D2O) d 6.82 (s, 2H), 4.08 (s, 4H), 4.02 (s, 2H), 4.00 (s, 2H), 3.73 (s, 2H), 3.53-3.45 (m, 6H), 3.26-3.21 (m, 6H), 1.60-1.49 (m, 4H), 1.30-1.22 (m, 2H); 13C NMR (101 MHz, D2O, as a TFA salt, the signals of TFA were not included) d 173.38, 172.85, 170.12, 170.05, 166.56, 134.26, 56.31, 55.72, 55.66, 53.83, 52.47, 50.11, 49.98, 39.31, 37.37, 27. 65, 27.21, 23.22. (0649) (0650) [0291] 2-[2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)ethyl]([6-(2,5- dioxo-2,5-dihydro-lH-pyrrol-l-yl)hexyl]carbamoyl}methyl)amino}acetic acid lOd was prepared as described above. Yield: 66 mg (26% referring to the linker) (calculated as TFA salt. TFA content: 1.73 ± 0.25 mol. Eq.), HPLC (method 2, 220 nm) 98%. LRMS-ESI (m/z) calcd. for C24H37N5O11 [M+H]+: 572.58. Found: 572.27. NMR (400 MHz, D2O) d 6.83 (s, 2H), 4.05 (s, 4H), 4.01 (s, 2H), 3.97 (s, 2H), 3.73 (s, 2H), 3.53-3.44 (m, 6H), 3.27-3.21 (m, 6H), 1.59-1.47 (m, 4H), 1.36-1.24 (m, 4H); 13C NMR (101 MHz, D2O, as a TFA salt, the signals of TFA were not included) d 173.41, 172.92, 169.89, 169.87, 166.34, 134.24, 56.28, 55.59, 55.56, 53.77, 52.58, 50.00, 49.93, 39.41, 37.44, 27.96, 27.43, 25.40, 25.39.
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