5,7-diamino-N⁵-benzyl-N⁵-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

Base Information

• Chemical Name: 5,7-diamino-N⁵-benzyl-N⁵-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine
• CAS No.: 128584-54-3
• Molecular Formula: C₂₉H₃₂BrN₅O₄
• Molecular Weight: 594.508

Synonyms:5,7-diamino-N⁵-benzyl-N⁵-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

Chemical Property of 5,7-diamino-N⁵-benzyl-N⁵-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

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Technology Process of 5,7-diamino-N⁵-benzyl-N⁵-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

There total 6 articles about 5,7-diamino-N⁵-benzyl-N⁵-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine 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: 80.0%

N-Benzyl-N-[2-(4-bromo-phenyl)-ethyl]-N'-[5-cyano-3-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3H-imidazol-4-yl]-acetamidine (128563-31-5) → 5,7-diamino-N5-benzyl-N5-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (128584-54-3)

Guidance literature:

With sodium hydride; In 1,4-dioxane; for 1.5h; Heating;

DOI:10.1139/v92-166

Reference yield:

4-Bromophenethylamine (73918-56-6) → 5,7-diamino-N5-benzyl-N5-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (128584-54-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 59 percent / borane-pyridine complex, acetic acid / petroleum ether / 2 h / Ambient temperature

2: 87 percent / triethylamine / CH₂Cl₂ / 18 h / Ambient temperature

3: phosphoryl chloride / acetonitrile / 48 h

4: ammonia / methanol

5: 80 percent / sodium hydride / dioxane / 1.5 h / Heating

With borane pyridine; ammonia; sodium hydride; acetic acid; triethylamine; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; acetonitrile; Petroleum ether;

DOI:10.1139/v92-166

Reference yield:

benzaldehyde (100-52-7) → 5,7-diamino-N5-benzyl-N5-<2-(4-bromophenyl)ethyl>-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (128584-54-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 59 percent / borane-pyridine complex, acetic acid / petroleum ether / 2 h / Ambient temperature

2: 87 percent / triethylamine / CH₂Cl₂ / 18 h / Ambient temperature

3: phosphoryl chloride / acetonitrile / 48 h

4: ammonia / methanol

5: 80 percent / sodium hydride / dioxane / 1.5 h / Heating

With borane pyridine; ammonia; sodium hydride; acetic acid; triethylamine; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; acetonitrile; Petroleum ether;

DOI:10.1139/v92-166

upstream raw materials:

N-Benzyl-N-[2-(4-bromo-phenyl)-ethyl]-N'-[5-cyano-3-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3H-imidazol-4-yl]-acetamidine

4-Bromophenethylamine

benzaldehyde

N-benzyl-2-(4-bromophenyl)ethanamine

Downstream raw materials:

5,7-diamino-N⁵-<2-<4-(2-carboxyethyl)phenyl>ethyl>-3-(β-D-ribofuranosyl)imidazo<4,5-b>pyridine dihydrochloride

7-amino-3-[2,3-O-(1-methylethylidene)-.β-D-ribofuranosyl]-N-{2-[p-(2-carboxyethyl)-phenyl]-ethyl}-3H-imidazo[4,5-b]-pyridin-5-amine

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