Metesind

Base Information

• Chemical Name: Metesind
• CAS No.: 138384-68-6
• Molecular Formula: C23H24N4O3S
• Molecular Weight: 436.534
• UNII: 2027T69J24
• DSSTox Substance ID: DTXSID90930100
• Nikkaji Number: J456.822B
• Wikidata: Q27253390
• NCI Thesaurus Code: C166526
• Pharos Ligand ID: RK9MFPC5YJRZ
• ChEMBL ID: CHEMBL9440
• Mol file: 138384-68-6.mol

Synonyms:AG 331;AG-331;N(6)-(4-(N-morpholinosulfonyl)benzyl)-N(6)-methyl-2,6-diaminobenz(cd)indole glucuronate

Chemical Property of Metesind

Chemical Property:

• PSA: 97.87000
• LogP: 4.01410
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 436.15691181
• Heavy Atom Count: 31
• Complexity: 768

Purity/Quality:

METESIND 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CC1=CC=C(C=C1)S(=O)(=O)N2CCOCC2)C3=C4C=CC=C5C4=C(C=C3)N=C5N
• Uses: Antineoplastic (specific thymidylate synthase inhibitor).

Technology Process of Metesind

There total 13 articles about Metesind 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:

1,8-naphtholactam (130-00-7) → (2-Imino-1,2-dihydro-benzo[cd]indol-6-yl)-methyl-[4-(morpholine-4-sulfonyl)-benzyl]-amine (138384-68-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 51 percent / 70percent HNO₃ / acetic acid / 1 h / 20 - 50 °C

2: H₂ / 5percent Pd/C / tetrahydrofuran / 16 h / 2068.6 Torr

3: 75 percent / DIEA / dimethylformamide / a) 105 deg C, 1.5 h, b) 85 deg C, 1.5 h

4: 59 percent / DIEA / dimethylformamide / 1.42 h / 75 °C

5: Lawesson's reagent / toluene

6: NaOH / tetrahydrofuran; ethanol

7: NH₃ / methanol

With Lawessons reagent; sodium hydroxide; ammonia; hydrogen; nitric acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00082a006

Reference yield:

N-hydroxy-4-nitro-1,8-naphthalimide (28434-96-0) → (2-Imino-1,2-dihydro-benzo[cd]indol-6-yl)-methyl-[4-(morpholine-4-sulfonyl)-benzyl]-amine (138384-68-6)

Guidance literature:

Multi-step reaction with 8 steps

1: Na₂CO₃ / H₂O / 1 h / Heating

2: NaOH / ethanol; H₂O / 16 h / 25 °C

3: H₂ / 5percent Pd/C / tetrahydrofuran / 16 h / 2068.6 Torr

4: 75 percent / DIEA / dimethylformamide / a) 105 deg C, 1.5 h, b) 85 deg C, 1.5 h

5: 59 percent / DIEA / dimethylformamide / 1.42 h / 75 °C

6: Lawesson's reagent / toluene

7: NaOH / tetrahydrofuran; ethanol

8: NH₃ / methanol

With Lawessons reagent; sodium hydroxide; ammonia; hydrogen; sodium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00082a006

Reference yield:

N-(2,4-dinitrophenoxy)-4-nitronaphthalimide (65300-66-5) → (2-Imino-1,2-dihydro-benzo[cd]indol-6-yl)-methyl-[4-(morpholine-4-sulfonyl)-benzyl]-amine (138384-68-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOH / ethanol; H₂O / 16 h / 25 °C

2: H₂ / 5percent Pd/C / tetrahydrofuran / 16 h / 2068.6 Torr

3: 75 percent / DIEA / dimethylformamide / a) 105 deg C, 1.5 h, b) 85 deg C, 1.5 h

4: 59 percent / DIEA / dimethylformamide / 1.42 h / 75 °C

5: Lawesson's reagent / toluene

6: NaOH / tetrahydrofuran; ethanol

7: NH₃ / methanol

With Lawessons reagent; sodium hydroxide; ammonia; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00082a006

upstream raw materials:

1,8-naphtholactam

6-aminobenzindol-2(1H)-one

N-(2,4-dinitrophenoxy)-4-nitronaphthalimide

N-hydroxy-4-nitro-1,8-naphthalimide

Refernces