CID 11016750

Base Information

• Chemical Name: CID 11016750
• CAS No.: 6576-51-8
• Molecular Formula: C22H27 N9 O4 . Cl H
• Molecular Weight: 517.975
• Mol file: 6576-51-8.mol

Synonyms:NSC150528

Chemical Property of CID 11016750

Chemical Property:

• Appearance/Colour: YELLOW TO YELLOW WITH A BROWN CAST POWDER
• Vapor Pressure: 9.91E-21mmHg at 25°C
• Melting Point: 184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer)
• Boiling Point: 715.4 °C at 760 mmHg
• Flash Point: 386.4 °C
• PSA: 181.06000
• LogP: 3.67870
• Storage Temp.: ?20°C
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 517.1952781
• Heavy Atom Count: 36
• Complexity: 819

Purity/Quality:

99% ^*data from raw suppliers

DISTAMYCIN A HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NC3=CN(C(=C3)C(=O)NCCC(=[NH2+])N)C)C)NC=O.[Cl-]
• Therapeutic Function: Antibiotic

Technology Process of CID 11016750

There total 25 articles about CID 11016750 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-methyl-4-nitro-pyrrol-2-carboxylic acid (13138-78-8) → distamycin A hydrochloride (6576-51-8)

Guidance literature:

Multi-step reaction with 7 steps

1: SOCl₂ / tetrahydrofuran / 0.08 h / Heating

2: Hunig's base / tetrahydrofuran / -20 - 20 °C

3: 1.) H₂, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C

4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature

5: 1.) HCl, 2.) NH₃ / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT

6: 70 percent / H₂ / 10percent Pd/C / methanol / 40 °C

7: methanol; tetrahydrofuran / 0.5 h / -40 °C

With hydrogenchloride; thionyl chloride; ammonia; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00220a019

Reference yield:

4-amino-1-methylpyrrole-2-carboxylic acid (45776-13-4) → distamycin A hydrochloride (6576-51-8)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature

2: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C

3: TFA / CH₂Cl₂

4: EDC / dimethylformamide / 40 °C

5: H₂ / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature

6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight

7: 1.) NaHCO₃, 2.) HCl / H₂O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00330a022

Reference yield:

ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate (2853-29-4) → distamycin A hydrochloride (6576-51-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating

2: H₂, 1.0 M Na₂CO₃(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature

3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature

4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C

5: TFA / CH₂Cl₂

6: EDC / dimethylformamide / 40 °C

7: H₂ / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature

8: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight

9: 1.) NaHCO₃, 2.) HCl / H₂O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight

With hydrogenchloride; sodium hydroxide; hydrogen; sodium hydrogencarbonate; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00330a022

upstream raw materials:

N-Succinimidyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

(1-amino-3-ammoniopropylidene)ammonium dihydrobromide

1-methyl-4-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamidopropionamidine hydrochloride

N-formylimidazole

Downstream raw materials:

C₂₃H₂₉N₉O₄

C₂₄H₃₁N₉O₄

N-(5-{[(5-{[(2-cyanoethyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide

Refernces

• 1、 Grehn, Leif,Ragnarsson, Ulf. "Novel Efficient Total Synthesis of Antiviral Antibiotic Distamycin A". . p. 3492 - 3497. Retrieved 2007/10/02.