(R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid

Base Information

• Chemical Name: (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid
• CAS No.: 1214265-80-1
• Molecular Formula: C₂₂H₂₂FN₇O₃
• Molecular Weight: 451.46
• Mol file: 1214265-80-1.mol

Synonyms:(R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid

Chemical Property of (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid

There total 5 articles about (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid 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: 65.0%

4-amino-2-fluoro-5-methoxy-benzoic acid (1001346-91-3) + (6R)-3-chloro-6-ethyl-5-(propan-2-yl)-5,6-dihydroimidazo[1,5-f]pteridine-7-carbonitrile (1214265-79-8) → (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid (1214265-80-1)

Guidance literature:

With N,N-dimethyl acetamide; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 160 ℃; Microwave irradiation;

DOI:10.1016/j.bmcl.2016.10.009

Reference yield:

methyl (2R)-2-[(2-chloro-5-nitropyrimidin-4-yl)(propan-2-yl)amino]butanoate (946161-16-6) → (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid (1214265-80-1)

Guidance literature:

Multi-step reaction with 4 steps

1: platinum on carbon; hydrogen; ammonium vanadate; triphenyl phosphite / 5 h / 20 °C / 3878.71 Torr

2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

3: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

4: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate; N,N-dimethyl acetamide / 1,4-dioxane / 160 °C / Microwave irradiation

With triphenyl phosphite; ammonium vanadate; N,N-dimethyl acetamide; platinum on carbon; hydrogen; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; 4: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2016.10.009

Reference yield:

(7R)-2-chloro-7-ethyl-8-(propan-2-yl)-7,8-dihydropteridin-6(5H)-one (889877-77-4) → (R)-4-(7-cyano-6-ethyl-5-isopropyl-5,6-dihydroimidazo[1,5-f]pteridin-3-ylamino)-2-fluoro-5-methoxybenzoic acid (1214265-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

2: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

3: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate; N,N-dimethyl acetamide / 1,4-dioxane / 160 °C / Microwave irradiation

With N,N-dimethyl acetamide; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; 3: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2016.10.009

upstream raw materials:

4-amino-2-fluoro-5-methoxy-benzoic acid

(6R)-3-chloro-6-ethyl-5-(propan-2-yl)-5,6-dihydroimidazo[1,5-f]pteridine-7-carbonitrile

Methyl (2R)-2-(isopropylamino) butanoate

methyl (2R)-2-[(2-chloro-5-nitropyrimidin-4-yl)(propan-2-yl)amino]butanoate

Refernces

• 1、 -. "DIHYDROIMIDAZO [ 1, 5-F] PTERIDINES AS POLO-LIKE KINASE INHIBITORS". Page/Page column 25. . Retrieved 2010/04/06.