4-[2-(5-{3-cyano-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

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Chemical Name:4-[2-(5-{3-cyano-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
CAS No.:1258975-66-4
Molecular Formula:C₂₂H₂₄N₆O₃S
Molecular Weight:452.537
Hs Code.:

Synonyms:4-[2-(5-{3-cyano-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

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Chemical Property of 4-[2-(5-{3-cyano-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

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Technology Process of 4-[2-(5-{3-cyano-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

There total 5 articles about 4-[2-(5-{3-cyano-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 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: 17.0%

: 1258976-26-9
ethyl 4-[2-(5-{3-cyano-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

: 1258975-66-4
4-[2-(5-{3-cyano-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

Guidance literature:: ethyl 4-[2-(5-{3-cyano-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; With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 20.5h;

With ammonium chloride; In tetrahydrofuran; water; ethyl acetate;

Reference yield:

: 258273-31-3
3-cyano-4-isopropoxybenzoic acid

: 1258975-66-4
4-[2-(5-{3-cyano-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

Guidance literature:: Multi-step reaction with 6 steps

1: trichlorophosphate / 3 h / 90 °C

2: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 1 h / 20 - 70 °C

3: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 1.5 h / 160 °C / Microwave irradiation

4: dichloromethane / 1.5 h / 20 °C / Inert atmosphere

5: potassium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C

6: lithium hydroxide / tetrahydrofuran; water / 20.5 h / 20 °C

With copper(l) iodide; tert.-butylnitrite; potassium carbonate; caesium carbonate; copper(ll) bromide; lithium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/acs.jmedchem.5b01512

Reference yield:

: 1258440-55-9
5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile

: 1258975-66-4
4-[2-(5-{3-cyano-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

Guidance literature:: Multi-step reaction with 5 steps

1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 1 h / 20 - 70 °C

2: copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 1.5 h / 160 °C / Microwave irradiation

3: dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4: potassium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C

5: lithium hydroxide / tetrahydrofuran; water / 20.5 h / 20 °C

With copper(l) iodide; tert.-butylnitrite; potassium carbonate; caesium carbonate; copper(ll) bromide; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/acs.jmedchem.5b01512