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[ CAS No. 1263045-16-4 ] {[proInfo.proName]}

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Chemical Structure| 1263045-16-4
Chemical Structure| 1263045-16-4
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Product Details of [ 1263045-16-4 ]

CAS No. :1263045-16-4 MDL No. :MFCD13184954
Formula : C18H28N2O9 Boiling Point : No data available
Linear Structure Formula :- InChI Key :IAJVEYLYYHOZEY-UHFFFAOYSA-N
M.W : 416.42 Pubchem ID :51340949
Synonyms :
Chemical Name :1-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3-oxo-7,10,13,16-tetraoxa-4-azanonadecan-19-oic acid

Safety of [ 1263045-16-4 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1263045-16-4 ]

* 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 [ 1263045-16-4 ]

[ 1263045-16-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1343407-40-8 ]
  • [ 1263045-16-4 ]
  • [ 1343407-44-2 ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃; Amine 10 (99 mg, 0.109 mmol, 1 eq) was added to a solution of NHS-PEG4-Maleimide (Thermo Scientific, 61.6 mg, 0.120 mmol, 1.1 eq) and TEA (18.2 μL, 0.130 mmol, 1.2 eq) in a mixture of anhydrous DCM (5 mL) and DMF (1 mL). The reaction was allowed to stir at room temperature overnight at which point it was found to be almost complete by LC/MS (3.27 min (ES+) m/z (relative intensity) 1307.55 ([M+H]+., 100)). The volatiles were removed by evaporation under reduced pressure. The residue was purified by flash chromatography (gradient from 3/97 up to 5/95 methanol/chloroform) to yield 71 mg (50%) of pure product 13.[0440]Analytical Data: 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 7.50 (d, 2H, J=8.47 Hz), 7.28 (s, 1H), 7.25-7.20 (m, 2H), 7.18-7.01 (m, 9H), 6.89 (d, 1H, J=7.58 Hz), 6.79 (d, 2H, J=8.68 Hz), 6.59 (s, 2H), 6.51 (s, 1H), 5.77 (d, 1H, J=6.42 Hz), 5.25 (d, 1H, J=11.43 Hz), 4.83-4.64 (m, 2H), 4.63-4.49 (m, 1H), 4.43-4.38 (m, 1H), 4.18 (s, 1H), 3.96-3.85 (m, 1H), 3.84 (s, 3H), 3.76-3.56 (m, 9H), 3.57-3.34 (m, 15H), 3.34-3.20 (m, 3H), 3.15 (dd, 1H, J=14.22 Hz, J=5.60 Hz), 3.07-2.89 (m, 4H), 2.48-2.29 (m, 4H), 1.97-1.90 (m, 1H), 1.61-1.39 (m, 3H), 1.35 (s, 9H), 1.29-1.12 (m, 4H). MS (ES+) m/z (relative intensity) 1307.55 ([M+H]+., 100).
  • 2
  • [ 756525-91-4 ]
  • [ 1263045-16-4 ]
  • 3
  • [ 55750-62-4 ]
  • [ 1615234-93-9 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-blc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.227g With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; [0277] Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
  • 4
  • [ 6066-82-6 ]
  • [ 1263045-16-4 ]
  • [ 756525-99-2 ]
YieldReaction ConditionsOperation in experiment
0.109 g With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-blc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.109 g With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Synthesis of linker-drugReferring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
0.109g With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; [0277] Referring to the scheme of synthesis of Compound O, β-alanine was treated with maleic anhydride in DMF and the acid so obtained was reacted with N-hydroxysuccinimide (NHS) under DCC coupling to give NHS-ester. The BOC protective group in commercially available t-boc-N-amido-dPEG4-acid was removed by treatment with TFA to give the TFA salt of the amine, which was reacted with previously synthesized NHS ester. The carboxylic acid so obtained was isolated and was coupled with N-hydroxysuccinimide using EDCI to furnish NHS ester Compound O.
330 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h; The product 4-11 (1.0 g, 2.4 mmol) obtained in the previous step and EDC-HCl (0.55 g, 2.88 mmol) were dissolved in 25 mL DCM, HOSu (0.33 g, 2.88 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. 50 mL water was added, the mixture was then extracted with EtOAc for 3 times (50 mL×3). The organic phases were combined, washed with saturated brine for 3 times (50 mL×3), dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by prep-HPLC to give 330 mg product as colorless oil, yield 27%. LCMS (ESI) m/z 514.2 (M+H)+.

  • 5
  • [ 1263045-16-4 ]
  • (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8'-(((5-(3-aminoprop-1-yn-1-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) [ No CAS ]
  • (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8′-(((5-(1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricos-22-yn-23-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; (b) (11S,11aS,11'S,11a'S)-di-tert-butyl 8,8'-(((5-(1-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-3,19-dioxo-7,10,13,16-tetraoxa-4,20-diazatricos-22-yn-23-yl)-1,3-phenylene)bis(methylene))bis(oxy))bis(7-methoxy-2-methylene-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate) (9) <strong>[1263045-16-4]MAL-dPEG4-acid</strong> (88 mg, 0.21 mmol) was added to a stirred solution of EDCI (41 mg, 0.21 mmol) and the crude primary amine 8 in dry DCM (4 mL) at room temperature. The reaction mixture was stirred under an argon atmosphere for 3 hours at which point analysis by LC/MS showed a substantial amount of desired product at retention time 3.58 min (ES+) m/z 1475 ([M+H]+, ?10% relative intensity), 1498 ([M+Na]+, ?5% relative intensity) accompanied by a side product at retention time 3.85 min. The reaction mixture was diluted with DCM (30 mL) and washed with H2O (3*10 mL), brine (20 mL), dried (MgSO4), filtered and evaporated in vacuo to provide the crude product. Purification by flash chromatography (gradient elution: 100% DCM to 96:4 v/v DCM/MeOH) gave the maleimide 9 as a foam (67 mg, 22% yield over 2 steps).
67 mg With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; <strong>[1263045-16-4]MAL-dPEG4-acid</strong> (88 mg, 0.21 mmol) was added to a stirred solution of EDCI (41 mg, 0.21 mmol) and the crude primary amine 8 in dry DCM (4 mL) at room temperature. The reaction mixture was stirred under an argon atmosphere for 3 hours at which point analysis by LC/MS showed a substantial amount of desired product at retention time 3.58 min (ES+) mlz 1475 ([M+ H]+ , -10% relative intensity), 1498 ([M+ Na]+', -5% relative intensity) accompanied by a side product at retention time 3.85 min. The reaction mixture was diluted with DCM (30 mL) and washed with H20 (3 x 10 mL), brine (20 mL), dried (MgS04), filtered and evaporated in vacuo to provide the crude product. Purification by flash chromatography (gradient elution: 100% DCM to 96:4 v/v DCM/MeOH) gave the maleimide 9 as a foam (67 m 22% yield over 2 steps).
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