FG-4592 interMediate

Base Information

• Chemical Name: FG-4592 interMediate
• CAS No.: 1455091-10-7
• Molecular Formula: C18H15NO4
• Molecular Weight: 295.295
• Mol file: 1455091-10-7.mol

Synonyms:FG-4592 interMediate;4-Hydroxy-7-phenoxy-3-isoquinolinecarboxylic acid methyl ester;methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Chemical Property of FG-4592 interMediate

Chemical Property:

• Boiling Point: 534.7±45.0 °C(Predicted)
• PKA: 5.80±0.50(Predicted)
• PSA: 68.65000
• Density: 1.320±0.06 g/cm3(Predicted)
• LogP: 3.51930
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl4-Hydroxy-7-phenoxyisoquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 4-Hydroxy-7-phenoxyisoquinoline-3-carboxylate is an intermediate of N-[(4-Hydroxy-1-methyl-7-phenoxy-3-isoquinolinyl)carbonyl]glycine (H948180), a hypoxia-inducible factor (HIF) prolyl hydroxylase inhibitor used to increase white blood cell levels in blood and hematopoietic progenitor cells in bone marrow.

Technology Process of FG-4592 interMediate

There total 11 articles about FG-4592 interMediate 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%

2-{[(methoxycarbonylmethyl)(toluene-4-sulfonyl)amino]methyl}-4-phenoxybenzoic acid methyl ester (1455091-06-1) → 4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid methyl ester (1455091-10-7)

Guidance literature:

With methanol; sodium methylate; for 2h;

Reference yield: 72.5%

2-(chloromethyl)-4-phenoxybenzoic acid methyl ester (1455091-04-9) + methyl tosylglycinate (2645-02-5) → 4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid methyl ester (1455091-10-7)

Guidance literature:

2-(chloromethyl)-4-phenoxybenzoic acid methyl ester; methyl tosylglycinate; With sodium methylate; potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 50 ℃; for 1h; Inert atmosphere;

With sodium methylate; In methanol; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

Reference yield:

2-(chloromethyl)-4-phenoxybenzoic acid methyl ester (1455091-04-9) → 4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid methyl ester (1455091-10-7)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 50 °C

2: sodium methylate / dimethyl sulfoxide; methanol / 0.5 h / 20 °C

With sodium methylate; potassium carbonate; sodium iodide; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

2-(chloromethyl)-4-phenoxybenzoic acid methyl ester

2-{[(methoxycarbonylmethyl)(toluene-4-sulfonyl)amino]methyl}-4-phenoxybenzoic acid methyl ester

5-bromophthalide

phenol

Downstream raw materials:

3-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2,2-dimethylpropionic acid ethyl ester

4-hydroxy-1-methyl-7-phenoxyisoquinolinyl-3-carboxylic acid methyl ester

3-[(4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carbonyl)amino]propionic acid

2-(S)-amino-3-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propionic acid

Refernces

• 1、 -. "Isoquinolone compound and application thereof". Paragraph 0199; 0200; 0205; 0206. . Retrieved 2018/09/08.
• 2、 -. "PROCESS FOR MAKING ISOQUINOLINE COMPOUNDS". Paragraph 0236. . Retrieved 2014/02/15.