(4-aminophenyl)(2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(3aH)-yl)methanone

Base Information

• Chemical Name: (4-aminophenyl)(2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(3aH)-yl)methanone
• CAS No.: 195531-22-7
• Molecular Formula: C19H18N4O
• Molecular Weight: 318.378
• Mol file: 195531-22-7.mol

Synonyms:(4-aminophenyl)(2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(3aH)-yl)methanone;(4-aminophenyl)(9-chloro-2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(1H)-yl)methanone

Chemical Property of (4-aminophenyl)(2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(3aH)-yl)methanone

Chemical Property:

• PSA: 75.01000
• LogP: 3.81640

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4-aminophenyl)(2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(3aH)-yl)methanone

There total 13 articles about (4-aminophenyl)(2-methyl-4,5-dihydrobenzo[b]imidazo[4,5-d]azepin-6(3aH)-yl)methanone 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: 94.0%

2-methyl-6-(4-nitrobenzoyl)-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine monohydrochloride → {4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine (195531-22-7)

Guidance literature:

With hydrogen; nickel; In methanol; at 25 ℃; for 1h;

DOI:10.3987/COM-04-10025

Reference yield: 94.0%

2-methyl-6-(4-nitrobenzoyl)-1,4,5,6-tetrahydroimidazo-[4,5-d][1]benzazepine (168626-71-9) → {4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine (195531-22-7)

Guidance literature:

With hydrogen; In methanol; N,N-dimethyl-formamide; at 25 ℃; for 1h; Reagent/catalyst;

DOI:10.1021/op034079e

Reference yield:

1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile (68595-19-7) → {4-[(2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl)carbonyl]phenyl}amine (195531-22-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / acetic acid; cc. HCl / 11 h / 80 °C

2: 89 percent / pyridinium hydrobromide perbromide / CHCl₃ / 1 h / 15 - 30 °C

3: 28 percent / potassium carbonate / CHCl₃ / 96 h / Heating

4: 61 percent / cc. sulfuric acid / acetic acid / 51 h / 70 °C

5: 73 percent / pyridine monohydrochloride / dimethylformamide / 3 h / 25 °C

6: 94 percent / H₂ / Raney nickel / methanol / 1 h / 25 °C

With hydrogenchloride; sulfuric acid; hydrogen; pyridine hydrochloride; pyridinium hydrobromide perbromide; potassium carbonate; acetic acid; nickel; In methanol; chloroform; acetic acid; N,N-dimethyl-formamide;

DOI:10.3987/COM-04-10025

upstream raw materials:

4-bromo-1-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one

methyl N-tosylanthranilate

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

1-[(4-methylphenyl)sulfonyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carbonitrile

Downstream raw materials:

conivaptan hydrochloride

Refernces

• 1、 Tsunoda, Takashi,Yamazaki, Atsuki,Iwamoto, Hidenori,Sakamoto, Shuichi. "Practical Synthesis of N-{4-[(2-Methyl-4,5-dihydroimidazo[4,5-d][1] benzazepin-6(1H)-yl)carbonyl]phenyl}biphenyl-2-carboxamide Monohydrochloride: An Arginine Vasopressin Antagonist". . p. 883 - 887. Retrieved 2013/09/05.