AMG 511

Base Information

• Chemical Name: AMG 511
• CAS No.: 1253573-53-3
• Molecular Formula: C₂₂H₂₈FN₉O₃S
• Molecular Weight: 517.587

Synonyms:

Chemical Property of AMG 511

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

AMG-511 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: AMG-511 is a PI3Kα inhibitor used as a cancer therapeutic due to its effect on cell growth and cell survival.

Technology Process of AMG 511

There total 12 articles about AMG 511 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: 52.0%

(R)-N,N-bis(4-methoxybenzyl)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (1253573-54-4) → AMG 511 (1253573-53-3)

Guidance literature:

(R)-N,N-bis(4-methoxybenzyl)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine; With trifluorormethanesulfonic acid; trifluoroacetic acid; at 70 ℃; for 2h;

With sodium hydrogencarbonate; sodium hydroxide; In water; at 0 ℃; pH=9;

Reference yield:

4-(2-((5-fluoro-6-methoxypyridin-3-yl)amino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (1253571-11-7) → (S)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (1253571-30-0) + AMG 511 (1253573-53-3)

Guidance literature:

With Chiralcel OJ-H; In methanol; carbon dioxide; at 40 ℃; Purification / work up; Resolution of racemate;

Reference yield:

5-fluoro-6-methoxypyridin-3-ylamine (886372-63-0) → (S)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (1253571-30-0) + AMG 511 (1253573-53-3)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / Cooling with ice; Inert atmosphere

2: hydrogenchloride; water / tetrahydrofuran; methanol / 0.17 h / 20 °C / Inert atmosphere

3: tetrahydrofuran; diethyl ether / 0.42 h / 0 °C

4: triethylamine / dichloromethane / 2 h

5: triethylamine / dichloromethane / 20 °C / Inert atmosphere

6: trifluoroacetic acid / 16 h / 75 °C

7: Chiralcel OJ-H column / Resolution of racemate

With hydrogenchloride; water; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm300846z

upstream raw materials:

4-(2-((5-fluoro-6-methoxypyridin-3-yl)amino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

(R)-N,N-bis(4-methoxybenzyl)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

4-(5-chloro-2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

5-(4-(bis(4-methoxybenzyl)-amino)-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxypyridin-3-yl)amino)nicotinaldehyde

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