(3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

Base Information

• Chemical Name: (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile
• CAS No.: 1311269-32-5
• Molecular Formula: C₂₉H₂₉N₅O₄S
• Molecular Weight: 543.646

Synonyms:(3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

Chemical Property of (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

Chemical Property:

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Technology Process of (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

There total 7 articles about (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile 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%

(3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile (1311269-28-9) + N-methyl-2-imidazolcarboxaldehyde (13750-81-7) → (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile (1311269-32-5)

Guidance literature:

(3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile; N-methyl-2-imidazolcarboxaldehyde; With trifluoroacetic acid; trifluoroacetic anhydride; In toluene; at 20 ℃; for 2h; Inert atmosphere;

With triethylsilane; In toluene; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jm300624s

Reference yield: 83.0%

1-methylimidazole-5-carbaldehyde (39021-62-0) + (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile (1311269-28-9) → (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile (1311269-32-5)

Guidance literature:

1-methylimidazole-5-carbaldehyde; (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile; With trifluoroacetic acid; trifluoroacetic anhydride; In toluene; at 20 - 30 ℃; for 2h; Inert atmosphere;

With triethylsilane; In toluene; at 20 ℃; Iknert atmosphere;

DOI:10.1002/anie.201101210

Reference yield:

(3R)-3-[(4-hydroxyphenyl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile (1311269-30-3) → (3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile (1311269-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid; trifluoroacetic anhydride / toluene / 2 h / 20 - 30 °C / Inert atmosphere

2.2: 20 °C / Iknert atmosphere

With pyridine; trifluoroacetic acid; trifluoroacetic anhydride; In toluene;

DOI:10.1002/anie.201101210

upstream raw materials:

1-methylimidazole-5-carbaldehyde

(3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

(3R)-7-bromo-3-[(4-hydroxyphenyl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione

(3R)-3-[(4-hydroxyphenyl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

Downstream raw materials:

(3R)-3-[(4-butoxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carbonitrile

5-[(3R)-3-[(4-hydroxyphenyl)methyl]-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-7-yl]furan-2-carbonitrile

4-{[(3R)-7-(3-chlorophenyl)-4-[(4-methoxybenzene)sulfonyl]-1-[(1-methyl-1H-imidazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl]methyl}phenyl N-benzylcarbamate

(R)-4-((7-(4-chlorophenyl)-4-(4-methoxyphenylsulfonyl)-1-((1-methyl-1H-imidazol-5-yl)methyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-3-yl)methyl)phenol

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