5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Base Information

• Chemical Name: 5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine
• CAS No.: 192513-61-4
• Molecular Formula: C24H27ClN2O3
• Molecular Weight: 426.943
• DSSTox Substance ID: DTXSID301120583
• Mol file: 192513-61-4.mol

Synonyms:SCHEMBL6601392;GMIXLJAGQVZZLD-UHFFFAOYSA-N;DTXSID301120583;192513-61-4;5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine;Methyl 1-[2-chloro-4-(1-pyrrolidinyl)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine-5-acetate

Chemical Property of 5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Chemical Property:

• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 426.1710204
• Heavy Atom Count: 30
• Complexity: 609

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC1CCCN(C2=CC=CC=C12)C(=O)C3=C(C=C(C=C3)N4CCCC4)Cl

Technology Process of 5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

There total 5 articles about 5-Methoxycarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine 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-pyrrolidin-2-one (872-50-4,26138-58-9) + 2-chloro-(4-pyrrolidin-1-yl) benzoic acid (192513-60-3) + methyl 2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylacetate (192513-58-9) → methyl [1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl] acetate (192513-61-4)

Guidance literature:

With pyridine; thionyl chloride; In methanol; dichloromethane;

Reference yield:

2-chloro-4-pyrrolidin-1-ylbenzoyl chloride (911312-93-1) + methyl 2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylacetate (192513-58-9) → methyl [1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl] acetate (192513-61-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jm020133q

Reference yield:

1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (24310-36-9) → methyl [1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl] acetate (192513-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 - 5 °C

1.2: 98 percent / tetrahydrofuran / 20 °C

2.1: 96 percent / Mg / 20 °C

3.1: 55 g / Et₃N / CH₂Cl₂ / 20 °C

With sodium hydride; magnesium; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Horner-Emmons reaction;

DOI:10.1021/jm020133q

upstream raw materials:

2-chloro-4-pyrrolidin-1-ylbenzoyl chloride

methyl 2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylacetate

1-tosyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

2-chloro-(4-pyrrolidin-1-yl) benzoic acid

Downstream raw materials:

(1R)-1-methylhexyl (5R)-[1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl]acetate

OPC 51803

(5R)-[1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl]acetic acid

[1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl] acetic acid