5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

Base Information

• Chemical Name: 5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine
• CAS No.: 144945-17-5
• Molecular Formula: C₂₃H₂₈FN₅O₄
• Molecular Weight: 457.505

Synonyms:5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

Chemical Property of 5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

Chemical Property:

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Technology Process of 5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

There total 6 articles about 5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-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: 56.0%

5,7-diamino-N5-benzyl-N5-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (144945-16-4) → 5,7-diamino-N5-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (144945-17-5)

Guidance literature:

With hydrogenchloride; hydrogen; palladium dihydroxide; In ethanol; for 6h; under 2585.7 Torr; Ambient temperature;

DOI:10.1139/v92-166

Reference yield:

4-fluoro-2-phenethylamine (1583-88-6) → 5,7-diamino-N5-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (144945-17-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 44 percent / borane-pyridine complex, acetic acid / petroleum ether / 2 h / Ambient temperature

2: 83 percent / triethylamine / CH₂Cl₂ / Ambient temperature

3: 41 percent / phosphoryl chloride / acetonitrile / 48 h

4: ammonia / methanol

5: 42 percent / sodium hydride / dioxane / 2 h / Heating

6: 56 percent / H₂, 1 N hydrochloric acid / palladium hydroxide / aq. ethanol / 6 h / 2585.7 Torr / Ambient temperature

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

DOI:10.1139/v92-166

Reference yield:

N-benzyl-2-(4-fluorophenyl)ethylamine (133715-32-9) → 5,7-diamino-N5-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine (144945-17-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / triethylamine / CH₂Cl₂ / Ambient temperature

2: 41 percent / phosphoryl chloride / acetonitrile / 48 h

3: ammonia / methanol

4: 42 percent / sodium hydride / dioxane / 2 h / Heating

5: 56 percent / H₂, 1 N hydrochloric acid / palladium hydroxide / aq. ethanol / 6 h / 2585.7 Torr / Ambient temperature

With hydrogenchloride; ammonia; hydrogen; sodium hydride; triethylamine; trichlorophosphate; palladium dihydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1139/v92-166

upstream raw materials:

5,7-diamino-N⁵-benzyl-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-<2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl>imidazo<4,5-b>pyridine

4-fluoro-2-phenethylamine

N-benzyl-2-(4-fluorophenyl)ethylamine

N-benzyl-N-propionyl-2-(4-fluorophenyl)ethylamine

Downstream raw materials:

N⁵-[2-(4-Fluoro-phenyl)-ethyl]-6-methyl-3H-imidazo[4,5-b]pyridine-5,7-diamine

5,7-diamino-N⁵-<2-(4-fluorophenyl)ethyl>-6-methyl-3-(β-D-ribofuranosyl)imidazo<4,5-b>pyridine

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