7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide

Base Information

• Chemical Name: 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide
• CAS No.: 362604-28-2
• Molecular Formula: C₂₁H₁₇ClN₄O₃S
• Molecular Weight: 440.91
• Mol file: 362604-28-2.mol

Synonyms:7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide

Chemical Property of 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide

There total 4 articles about 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide 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: 90.0%

7-chloro-2-oxo-3-(3,4,5-trimethyl-phenyl)-4-(2-trimethylsilanyl-ethoxy)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide (808172-36-3) → 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide (362604-28-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2004.08.056

Reference yield:

6-carbomethoxy-7-chloro-4-hydroxy-3-(3,4,5-trimethylphenyl)-1H-quinolin-2-one (335293-17-9) → 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide (362604-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 35 percent / PPh₃; DEAD / tetrahydrofuran

2: 85 percent / aq. LiOH / ethanol

3: 90 percent / DiPEA; EDAC; HOBt / CH₂Cl₂

4: 90 percent / TBAF / tetrahydrofuran

With lithium hydroxide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; 1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2004.08.056

Reference yield:

7-chloro-2-oxo-3-(3,4,5-trimethyl-phenyl)-4-(2-trimethylsilanyl-ethoxy)-1,2-dihydro-quinoline-6-carboxylic acid methyl ester (808172-29-4) → 7-chloro-4-hydroxy-2-oxo-3-(3,4,5-trimethyl-phenyl)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide (362604-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / aq. LiOH / ethanol

2: 90 percent / DiPEA; EDAC; HOBt / CH₂Cl₂

3: 90 percent / TBAF / tetrahydrofuran

With lithium hydroxide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.bmcl.2004.08.056

upstream raw materials:

7-chloro-2-oxo-3-(3,4,5-trimethyl-phenyl)-4-(2-trimethylsilanyl-ethoxy)-1,2-dihydro-quinoline-6-carboxylic acid [1,2,5]thiadiazol-3-ylamide

6-carbomethoxy-7-chloro-4-hydroxy-3-(3,4,5-trimethylphenyl)-1H-quinolin-2-one

7-chloro-2-oxo-3-(3,4,5-trimethyl-phenyl)-4-(2-trimethylsilanyl-ethoxy)-1,2-dihydro-quinoline-6-carboxylic acid methyl ester

7-chloro-2-oxo-3-(3,4,5-trimethyl-phenyl)-4-(2-trimethylsilanyl-ethoxy)-1,2-dihydro-quinoline-6-carboxylic acid