AMG 487

Base Information

• Chemical Name: AMG 487
• CAS No.: 473719-41-4
• Molecular Formula: C₃₂H₂₈F₃N₅O₄
• Molecular Weight: 603.601
• Mol file: 473719-41-4.mol

Synonyms:N-[(1R)-1-[3-(4-ethoxyphenyl)-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-N-(pyridin-3-ylmethyl)-2-[4-(trifluoromethoxy)phenyl]acetamide;Benzeneacetamide, N-((1R)-1-(3-(4-ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl)ethyl)-N-(3-pyridinylmethyl)-4-(trifluoromethoxy)-;

Chemical Property of AMG 487

Chemical Property:

• PSA: 99.44000
• LogP: 5.80550
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

AMG487 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(1R)-1-[3-(4-Ethoxyphenyl)-3,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-N-(3-pyridinylmethyl)-4-(trifluoromethoxy)benzeneacetamide is a selective and potent antagonist of the chemokine receptor CXCR3.

Technology Process of AMG 487

There total 12 articles about AMG 487 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: 57.0%

rac-3-(4-ethoxy-phenyl)-2-{1-[(pyridin-3-ylmethyl)-amino]-ethyl}-3H-pyrido[2,3-d]pyrimidin-4-one (947536-02-9) + 4-(trifluoromethoxy)phenylacetic acid (4315-07-5) → (+/-)-AMG487 (473719-41-4,473720-30-8)

Guidance literature:

4-(trifluoromethoxy)phenylacetic acid; With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

rac-3-(4-ethoxy-phenyl)-2-{1-[(pyridin-3-ylmethyl)-amino]-ethyl}-3H-pyrido[2,3-d]pyrimidin-4-one; In N,N-dimethyl-formamide; at 45 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201200184

Reference yield:

C23H23N5O2 (473720-92-2) + 4-(trifluoromethoxy)phenylacetic acid (4315-07-5) → AMG 487 (473719-41-4,473720-30-8)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2007.03.106

Reference yield:

(R)-{1-[3-(4-ethoxy-phenyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester (752244-95-4) → AMG 487 (473719-41-4,473720-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA / CH₂Cl₂ / 2 h / 20 °C

2: Na(OAc)3BH / 1,2-dichloro-ethane / 2 h / 20 °C

3: EDC; HOBt / dimethylformamide / 1 h / 20 °C

With sodium tris(acetoxy)borohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2007.03.106

upstream raw materials:

rac-3-(4-ethoxy-phenyl)-2-{1-[(pyridin-3-ylmethyl)-amino]-ethyl}-3H-pyrido[2,3-d]pyrimidin-4-one

4-(trifluoromethoxy)phenylacetic acid

(R)-[1-(4-oxo-4H-pyrido[2,3-d][1,3]oxazin-2-yl)-ethyl]-carbamic acid tert-butyl ester

(R)-{1-[3-(4-ethoxy-phenylcarbamoyl)-pyridin-2-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

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