Devazepide

Base Information

• Chemical Name: Devazepide
• CAS No.: 103420-77-5
• Molecular Formula: C25H20 N4 O2
• Molecular Weight: 408.459
• European Community (EC) Number: 683-026-0
• UNII: JE6P7QY7NH
• DSSTox Substance ID: DTXSID2046092
• Nikkaji Number: J273.248C
• Wikipedia: Devazepide
• Wikidata: Q5266620
• NCI Thesaurus Code: C98235
• Pharos Ligand ID: 5276TGS26411
• Metabolomics Workbench ID: 53129
• ChEMBL ID: CHEMBL9506
• Mol file: 103420-77-5.mol

Synonyms:Devazepide;L 364,718;L-364,718;L364,718;MK 329;MK-329;MK329

Chemical Property of Devazepide

Chemical Property:

• Vapor Pressure: 6.56E-23mmHg at 25°C
• Boiling Point: 758.6°Cat760mmHg
• PKA: 13.25±0.40(Predicted)
• Flash Point: 412.6°C
• PSA: 77.56000
• Density: 1.31g/cm³
• LogP: 3.62930
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >5mg/mL
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 408.15862589
• Heavy Atom Count: 31
• Complexity: 716

Purity/Quality:

97% ^*data from raw suppliers

Devazepide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=NC(C1=O)NC(=O)C3=CC4=CC=CC=C4N3)C5=CC=CC=C5
• Isomeric SMILES: CN1C2=CC=CC=C2C(=N[C@@H](C1=O)NC(=O)C3=CC4=CC=CC=C4N3)C5=CC=CC=C5
• Uses: Antagonist (cholecystokinin). Devazepide has been used as a cholecystokinin receptor 1 (CCK1R) antagonist in human embryonic kidney 293T cells and in human pancreatic slices.

Technology Process of Devazepide

There total 10 articles about Devazepide 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: 83.0%

Indole-2-carbonyl chloride (58881-45-1) + (S)-3-amino-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one (103343-66-4) → devazepide (103420-77-5)

Guidance literature:

With triethylamine; In dichloromethane; for 0.25h;

DOI:10.1021/jm00120a002

Reference yield:

benzyl 2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate (108895-98-3) → devazepide (103420-77-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / HBr / acetic acid / 1.) 70 deg C, 20 min, 2.) 80 deg C, 20 min

2: Et₃N / acetonitrile / Heating

3: 93 percent / NaH / dimethylformamide / 1.) 0 - 5 deg C, 1.5 h, 2.) 1.5 h

4: 93 percent / HBr / CH₂Cl₂ / 0.5 h / 0 - 5 °C

5: EDC, HOBT, DIEA / CH₂Cl₂ / Ambient temperature

With hydrogen bromide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00108a044

Reference yield:

2-α-(benzyloxycarbonyl)glycinyl)amino>benzophenone (108895-97-2) → devazepide (103420-77-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NH₄OAc / acetic acid / Ambient temperature

2: 88 percent / HBr / acetic acid / 1.) 70 deg C, 20 min, 2.) 80 deg C, 20 min

3: Et₃N / acetonitrile / Heating

4: 93 percent / NaH / dimethylformamide / 1.) 0 - 5 deg C, 1.5 h, 2.) 1.5 h

5: 93 percent / HBr / CH₂Cl₂ / 0.5 h / 0 - 5 °C

6: EDC, HOBT, DIEA / CH₂Cl₂ / Ambient temperature

With ammonium acetate; hydrogen bromide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00108a044

upstream raw materials:

Indole-2-carbonyl chloride

(S)-3-amino-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

Indole-2-carboxylic acid

benzyl 2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamate