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Chemical Structure| 152120-55-3 Chemical Structure| 152120-55-3

Structure of 152120-55-3

Chemical Structure| 152120-55-3

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Product Details of [ 152120-55-3 ]

CAS No. :152120-55-3
Formula : C20H18N4O4
M.W : 378.38
SMILES Code : O=C(OCC1=CC=CC=C1)N=C(N2N=CC=C2)NC(OCC3=CC=CC=C3)=O
MDL No. :MFCD02683516

Safety of [ 152120-55-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 152120-55-3 ]

* 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 [ 152120-55-3 ]

[ 152120-55-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 152120-55-3 ]
  • [ 129999-60-6 ]
  • C24H30N4O5 [ No CAS ]
  • 2
  • C14H18N3O2Pol [ No CAS ]
  • [ 152120-55-3 ]
  • [ 125238-99-5 ]
  • [ 76-05-1 ]
  • [ 1573112-66-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: 3mmol of Fmoc-protected aminoacid was dissolved in DMF with 3mmol HBTU and 3mmol Cl-HOBt. After cooling themixture to about 0° C, 6mmol DIEPA was added in one portion and mixed thoroughly about 1min then transferred to microwave peptide reaction vessel containing 1mmol of Rink amide AM resin (Fmoc deprotected form). Reaction was carried out under micro wave radiation (30W, 60°C, 5min). Resin was drained and washed with DMF. Deprotection was carried out by adding 5-8ml 20percent piperidine in DMF and microwave assisted reacting for 3 min (20W, 50°C, twice) followed by washing with DCM and DMF and continuing to next amino acid coupling. Orthogonal protected diamino acid was coupled to resin bound peptide at designated position, Fmoc was removed by microwave assisted deprotection as described. After thoroughly washing, 2equiv. of 1b was added to the resin and pyridine was added at minimum volume which could dissolve 1b and swell the resin. The mixture was transferred to standard peptide synthesis vessel and allowed to rotation overnight. Reaction resin was drained and washed twice with DCM, combined filtrate was concentrated in vaco and directly added to other peptide resin which ought to be guanidinylated or recrystalled by ethyl ether to recover 1b. Resin was cleaved by adding 10mlof TFA:TESi:H2O(95:2.5:2.5) and allowed reacting for 2h. Resin was drained and filtrate was collected and concentrated in vaco followed by diluting with acetonitrile to 10mmol/ml concentration and adding 1 equiv. TEA to catalyze reaction.
  • 3
  • C32H51N8O7Pol [ No CAS ]
  • [ 152120-55-3 ]
  • [ 125238-99-5 ]
  • [ 76-05-1 ]
  • [ 1573112-70-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: 3mmol of Fmoc-protected aminoacid was dissolved in DMF with 3mmol HBTU and 3mmol Cl-HOBt. After cooling themixture to about 0° C, 6mmol DIEPA was added in one portion and mixed thoroughly about 1min then transferred to microwave peptide reaction vessel containing 1mmol of Rink amide AM resin (Fmoc deprotected form). Reaction was carried out under micro wave radiation (30W, 60°C, 5min). Resin was drained and washed with DMF. Deprotection was carried out by adding 5-8ml 20percent piperidine in DMF and microwave assisted reacting for 3 min (20W, 50°C, twice) followed by washing with DCM and DMF and continuing to next amino acid coupling. Orthogonal protected diamino acid was coupled to resin bound peptide at designated position, Fmoc was removed by microwave assisted deprotection as described. After thoroughly washing, 2equiv. of 1b was added to the resin and pyridine was added at minimum volume which could dissolve 1b and swell the resin. The mixture was transferred to standard peptide synthesis vessel and allowed to rotation overnight. Reaction resin was drained and washed twice with DCM, combined filtrate was concentrated in vaco and directly added to other peptide resin which ought to be guanidinylated or recrystalled by ethyl ether to recover 1b. Resin was cleaved by adding 10mlof TFA:TESi:H2O(95:2.5:2.5) and allowed reacting for 2h. Resin was drained and filtrate was collected and concentrated in vaco followed by diluting with acetonitrile to 10mmol/ml concentration and adding 1 equiv. TEA to catalyze reaction.
  • 4
  • C12H19N4O3Pol [ No CAS ]
  • [ 152120-55-3 ]
  • [ 125238-99-5 ]
  • [ 76-05-1 ]
  • [ 1573112-72-7 ]
YieldReaction ConditionsOperation in experiment
General procedure: 3mmol of Fmoc-protected aminoacid was dissolved in DMF with 3mmol HBTU and 3mmol Cl-HOBt. After cooling themixture to about 0° C, 6mmol DIEPA was added in one portion and mixed thoroughly about 1min then transferred to microwave peptide reaction vessel containing 1mmol of Rink amide AM resin (Fmoc deprotected form). Reaction was carried out under micro wave radiation (30W, 60°C, 5min). Resin was drained and washed with DMF. Deprotection was carried out by adding 5-8ml 20percent piperidine in DMF and microwave assisted reacting for 3 min (20W, 50°C, twice) followed by washing with DCM and DMF and continuing to next amino acid coupling. Orthogonal protected diamino acid was coupled to resin bound peptide at designated position, Fmoc was removed by microwave assisted deprotection as described. After thoroughly washing, 2equiv. of 1b was added to the resin and pyridine was added at minimum volume which could dissolve 1b and swell the resin. The mixture was transferred to standard peptide synthesis vessel and allowed to rotation overnight. Reaction resin was drained and washed twice with DCM, combined filtrate was concentrated in vaco and directly added to other peptide resin which ought to be guanidinylated or recrystalled by ethyl ether to recover 1b. Resin was cleaved by adding 10mlof TFA:TESi:H2O(95:2.5:2.5) and allowed reacting for 2h. Resin was drained and filtrate was collected and concentrated in vaco followed by diluting with acetonitrile to 10mmol/ml concentration and adding 1 equiv. TEA to catalyze reaction.
  • 5
  • C8H16N3O2Pol [ No CAS ]
  • [ 152120-55-3 ]
  • [ 125238-99-5 ]
  • [ 76-05-1 ]
  • [ 1573112-78-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: 3mmol of Fmoc-protected aminoacid was dissolved in DMF with 3mmol HBTU and 3mmol Cl-HOBt. After cooling themixture to about 0° C, 6mmol DIEPA was added in one portion and mixed thoroughly about 1min then transferred to microwave peptide reaction vessel containing 1mmol of Rink amide AM resin (Fmoc deprotected form). Reaction was carried out under micro wave radiation (30W, 60°C, 5min). Resin was drained and washed with DMF. Deprotection was carried out by adding 5-8ml 20percent piperidine in DMF and microwave assisted reacting for 3 min (20W, 50°C, twice) followed by washing with DCM and DMF and continuing to next amino acid coupling. Orthogonal protected diamino acid was coupled to resin bound peptide at designated position, Fmoc was removed by microwave assisted deprotection as described. After thoroughly washing, 2equiv. of 1b was added to the resin and pyridine was added at minimum volume which could dissolve 1b and swell the resin. The mixture was transferred to standard peptide synthesis vessel and allowed to rotation overnight. Reaction resin was drained and washed twice with DCM, combined filtrate was concentrated in vaco and directly added to other peptide resin which ought to be guanidinylated or recrystalled by ethyl ether to recover 1b. Resin was cleaved by adding 10mlof TFA:TESi:H2O(95:2.5:2.5) and allowed reacting for 2h. Resin was drained and filtrate was collected and concentrated in vaco followed by diluting with acetonitrile to 10mmol/ml concentration and adding 1 equiv. TEA to catalyze reaction.
  • 6
  • [ 152120-55-3 ]
  • [ 125238-99-5 ]
  • [ 76-05-1 ]
  • [ 1573112-63-6 ]
YieldReaction ConditionsOperation in experiment
95.2% 1.5mmol of Fmoc-Dab(Boc)-OH wasdissolved in dichloromethane(DCM) with 6mmol of N,N-diisopropanylethylamine (DIEPA) and transferred to a vesselcontaining 1mmol of 2-Cl-Trt resin. After 1.5h of rotating mixing, resin wasdrained by filtration followed by capping with MeOH:DIEPA:DCM(1:1:18, v:v)for 30min. Fmoc was removed by 20percent piperidine in DMF followed byguanidinylation with 2mmol of compound 1b in pyridine solution over night.Resin was drained and washed twice with DCM, combined filtration was evaporatedin vaco to recover unreacted 1b.Resin was cleaved by adding 10ml of TFA:TESi:H2O(95:2.5:2.5,v:v)and allowed reacting for 1.5h. Resin was drained and filtrate was collected andconcentrated in vaco and lyophilized to give 408mg (95.2percent) compound 3 as white powder. HRMS: 429.1769 calc.by C21H24N4O6 (M+H+),found 429.1768.
 

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