1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate
• CAS No.: 1258976-21-4
• Molecular Formula: C₂₂H₂₆ClN₅O₃S
• Molecular Weight: 475.999
• Mol file: 1258976-21-4.mol

Synonyms:1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate

Chemical Property of 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate

There total 4 articles about 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate 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: 34.0%

2-bromo-5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazole (1258440-64-0) + 2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester (230301-11-8,924869-27-2) → 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate (1258976-21-4) + 1,1-dimethylethyl 1-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate (1258976-22-5)

Guidance literature:

With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 160 ℃; for 1h; Microwave irradiation;

DOI:10.1021/acs.jmedchem.5b01512

Reference yield:

3-chloro-4-isopropoxy-benzoic acid (213598-07-3) → 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate (1258976-21-4)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16.5 h / 20 °C

2: trichlorophosphate / 19 h / 20 - 90 °C

3: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 1 h / 20 °C

4: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 1 h / 160 °C / Microwave irradiation

With copper(l) iodide; tert.-butylnitrite; oxalyl dichloride; caesium carbonate; N,N-dimethyl-formamide; copper(ll) bromide; trichlorophosphate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01512

Reference yield:

3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride (213767-19-2) → 1,1-dimethylethyl 2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo-[4,3-c]pyridine-5-carboxylate (1258976-21-4)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate / 19 h / 20 - 90 °C

2: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 1 h / 20 °C

3: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 1 h / 160 °C / Microwave irradiation

With copper(l) iodide; tert.-butylnitrite; caesium carbonate; copper(ll) bromide; trichlorophosphate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01512

upstream raw materials:

2-bromo-5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazole

2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester

3-chloro-4-isopropoxy-benzoic acid

3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride

Downstream raw materials:

ethyl 4-[2-(5-{3-chloro-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]-pyridin-5-yl]butanoate

4-[2-(5-{3-chloro-4-[(1-methylethyl)-oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]butanoic acid

3-[2-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-propanoic acid

2-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine trifluoroacetate