(2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)phenyl)-5H-pyrrolo(2,1-C)(1,4)benzodiazepin-10(11H)-ylmethanone

Base Information

• Chemical Name: (2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)phenyl)-5H-pyrrolo(2,1-C)(1,4)benzodiazepin-10(11H)-ylmethanone
• CAS No.: 220460-92-4
• Molecular Formula: C₂₃H₁₉ClN₄O
• Molecular Weight: 402.883
• UNII: CC7IZ88XD2
• Wikidata: Q27089151
• Pharos Ligand ID: Q684SBJ6T4GN
• ChEMBL ID: CHEMBL363910
• Mol file: 220460-92-4.mol

Synonyms:VNA-932;WAY-151932

Chemical Property of (2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)phenyl)-5H-pyrrolo(2,1-C)(1,4)benzodiazepin-10(11H)-ylmethanone

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 402.1247389
• Heavy Atom Count: 29
• Complexity: 603

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=NN(C=C1)C2=CC(=C(C=C2)C(=O)N3CC4=CC=CN4CC5=CC=CC=C53)Cl

Technology Process of (2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)phenyl)-5H-pyrrolo(2,1-C)(1,4)benzodiazepin-10(11H)-ylmethanone

There total 10 articles about (2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)phenyl)-5H-pyrrolo(2,1-C)(1,4)benzodiazepin-10(11H)-ylmethanone 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: 43.0%

10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine (22162-53-4) + 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid (220461-68-7) → VNA-932 (220460-92-4)

Guidance literature:

2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid; With 1-methyl-pyrrolidin-2-one; thionyl chloride; In dichloromethane; at 20 ℃; Inert atmosphere;

10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine; With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.8b00697

Reference yield:

2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid (220461-68-7) → VNA-932 (220460-92-4)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 18h;

Reference yield:

(2-Chloro-4-fluorophenyl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (220461-65-4) + 3-Methylpyrazole (1453-58-3) → VNA-932 (220460-92-4) + [2-chloro-4-(5-methyl-pyrazol-1-yl)-phenyl]-(5H,11H)-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl-methanone (220460-91-3)

Guidance literature:

3-Methylpyrazole; With sodium hydride; In DMF (N,N-dimethyl-formamide);

(2-Chloro-4-fluorophenyl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone; In DMF (N,N-dimethyl-formamide); at 125 ℃; for 18h;

upstream raw materials:

10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoyl chloride

2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid

(2-Chloro-4-fluorophenyl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone

Downstream raw materials:

[2-Chloro-4-(3-methyl-pyrazol-1-yl)-phenyl]-(3-dimethylaminomethyl-5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone

C₂₃H₁₉ClN₄O₂

(3-bromo-5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3-methyl-pyrazol-1-yl)-phenyl]-methanone

Refernces

• 1、 -. "TRICYCLIC VASOPRESSIN AGONISTS". Page 33-34. . Retrieved 2010/02/08.