Carzelesin

Base Information

• Chemical Name: Carzelesin
• CAS No.: 119813-10-4
• Molecular Formula: C41H37 Cl N6 O5
• Molecular Weight: 729.235
• UNII: 668UF07O1P
• DSSTox Substance ID: DTXSID30152602
• Wikidata: Q27263977
• NCI Thesaurus Code: C1441
• ChEMBL ID: CHEMBL32911
• Mol file: 119813-10-4.mol

Synonyms:carzelesin;NSC 619029;U 80244;U-80244

Chemical Property of Carzelesin

Chemical Property:

• Boiling Point: 938.9°Cat760mmHg
• Flash Point: 521.6°C
• PSA: 135.70000
• Density: 1.426g/cm³
• LogP: 9.60700
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 728.2513960
• Heavy Atom Count: 53
• Complexity: 1320

Purity/Quality:

97% ^*data from raw suppliers

CARZELESIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C1=CC2=C(C=C1)C=C(O2)C(=O)NC3=CC4=C(C=C3)NC(=C4)C(=O)N5CC(C6=C7C(=CNC7=C(C=C65)OC(=O)NC8=CC=CC=C8)C)CCl
• Isomeric SMILES: CCN(CC)C1=CC2=C(C=C1)C=C(O2)C(=O)NC3=CC4=C(C=C3)NC(=C4)C(=O)N5C[C@H](C6=C7C(=CNC7=C(C=C65)OC(=O)NC8=CC=CC=C8)C)CCl
• Uses: Antineoplastic.

Technology Process of Carzelesin

There total 8 articles about Carzelesin 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: 89.0%

phenyl isocyanate (103-71-9) + 6-Diethylamino-benzofuran-2-carboxylic acid [2-((S)-1-chloromethyl-5-hydroxy-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide (119813-16-0) → carzelesin (119813-10-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.3987/COM-97-7920

Reference yield:

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6) → carzelesin (119813-10-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / PPh₃, CCl₄ / CH₂Cl₂ / 7 h / Ambient temperature

2: 88 percent / 25percent HCO₂NH₄ / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C

3: 3M HCl / ethyl acetate / 1 h / Ambient temperature

4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

5: 89 percent / NEt₃ / tetrahydrofuran / 18 h / Ambient temperature

With hydrogenchloride; tetrachloromethane; ammonium formate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 10% palladium on active carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-7920

Reference yield:

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (110314-50-6) → carzelesin (119813-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / 25percent HCO₂NH₄ / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C

2: 3M HCl / ethyl acetate / 1 h / Ambient temperature

3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

4: 89 percent / NEt₃ / tetrahydrofuran / 18 h / Ambient temperature

With hydrogenchloride; ammonium formate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 10% palladium on active carbon; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-7920

upstream raw materials:

phenyl isocyanate

6-Diethylamino-benzofuran-2-carboxylic acid [2-((S)-1-chloromethyl-5-hydroxy-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

Downstream raw materials:

aniline

U-76,074

6-Diethylamino-benzofuran-2-carboxylic acid [2-((S)-1-chloromethyl-5-hydroxy-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl]-amide

Refernces