6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]pyridine-3-carboxylic acid

Base Information

• Chemical Name: 6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]pyridine-3-carboxylic acid
• CAS No.: 893397-44-9
• Molecular Formula: C26H19Cl2N5O4
• Molecular Weight: 536.374
• UNII: N4LDS4H73C
• ChEMBL ID: CHEMBL1098726
• Pharos Ligand ID: 6H8FHGTP2GRX,BABYCQZN8VVM
• Wikidata: Q27284548
• Mol file: 893397-44-9.mol

Synonyms:BMS-688521;893397-44-9;N4LDS4H73C;CHEMBL1098726;6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]pyridine-3-carboxylic acid;3-Pyridinecarboxylic acid, 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro(4.4)non-7-yl)-;6-((5S,9R)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinic Acid;UNII-N4LDS4H73C;BJZ;SCHEMBL5259700;BDBM50318220;AKOS015994664;KE-0042;6-[(5S,9R)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4,4]non-7-yl]-3-pyridinecarboxylic acid;HY-10596;CS-0002663;Q27284548;6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl]pyridine-3-carboxylic acid

Chemical Property of 6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]pyridine-3-carboxylic acid

Chemical Property:

• PSA: 117.84000
• LogP: 4.46738
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 535.0814095
• Heavy Atom Count: 37
• Complexity: 971

Purity/Quality:

98% ^*data from raw suppliers

BMS688521 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)N(C(=O)C12CN(CC2C3=CC=C(C=C3)C#N)C4=NC=C(C=C4)C(=O)O)C5=CC(=CC(=C5)Cl)Cl
• Isomeric SMILES: CN1C(=O)N(C(=O)[C@]12CN(C[C@H]2C3=CC=C(C=C3)C#N)C4=NC=C(C=C4)C(=O)O)C5=CC(=CC(=C5)Cl)Cl

Technology Process of 6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]pyridine-3-carboxylic acid

There total 10 articles about 6-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]pyridine-3-carboxylic 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: 98.0%

4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile (509083-73-2) + 6-Chloro-3-pyridinecarboxylic acid (5326-23-8) → BMS-688521 (893397-44-9)

Guidance literature:

6-Chloro-3-pyridinecarboxylic acid; With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In ISOPROPYLAMIDE; for 3h; Heating / reflux;

4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile; In ISOPROPYLAMIDE; at 95 ℃; for 30h;

With water; In ISOPROPYLAMIDE; at 0 ℃; Product distribution / selectivity;

Reference yield: 85.4%

tert-butyl 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinate p-TSA salt → BMS-688521 (893397-44-9)

Guidance literature:

tert-butyl 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinate p-TSA salt; With sodium hydroxide; In tetrahydrofuran; tert-butyl methyl ether; water; at 30 ℃; Large scale reaction;

With hydrogenchloride; acetic acid; In water; toluene;

DOI:10.1021/op100225g

Reference yield: 75.0%

4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile (509083-73-2) + 6-iodo-nicotinic acid (13054-02-9) → BMS-688521 (893397-44-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ISOPROPYLAMIDE; at 110 ℃; for 16h; Product distribution / selectivity;

upstream raw materials:

4-((5S,9R)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro-[4.4]nonan-9-yl)benzonitrile

6-Chloro-3-pyridinecarboxylic acid

6-iodo-nicotinic acid

6-chloronicotinic acid trimethylsilyl ester

Refernces

• 1、 Zhang, Huiping,Watterson, Scott H.,Xiao, Zili,Dhar, T. G. Murali,Balasubramanian, Balu,Barrish, Joel C.,Chen, Bang-Chi. "A new and efficient synthesis of 6-[(5 S,9 R)-9-(4-Cyanophenyl)-3-(3,5- dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-yl]nicotinic acid, a potent LFA-1/ICAM inhibitor". experimental part. p. 936 - 938. Retrieved 2011/03/20.