5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide

Base Information

• Chemical Name: 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide
• CAS No.: 1403963-87-0
• Molecular Formula: C₁₇H₁₁Cl₂N₅OS
• Molecular Weight: 404.279

Synonyms:5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide

Chemical Property of 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide

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Technology Process of 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide

There total 5 articles about 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide 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: 62.0%

5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (1224944-47-1) + 4-(3-chlorophenyl)-2-methylthiazol-5-ylamine (1247687-32-6) → 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide (1403963-87-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jm3012239

Reference yield:

α-amino-(3-chlorophenyl)acetonitrile hydrochloride (49704-72-5) → 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide (1403963-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; sulfur / ethanol / 2.5 h / 0 - 60 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C

With sulfur; triethylamine; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;

DOI:10.1021/jm3012239

Reference yield:

methyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1224944-45-9) → 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chlorophenyl)-2-methylthiazol-5-yl]amide (1403963-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hydroxide; water / 3 h / 20 °C

2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / 2 h / Reflux

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C

With water; N-ethyl-N,N-diisopropylamine; lithium hydroxide; trichlorophosphate; In dichloromethane;

DOI:10.1021/jm3012239

upstream raw materials:

α-amino-(3-chlorophenyl)acetonitrile hydrochloride

3-iodopyrazolo[1,5-a]pyrimidin-5(4H)-one

methyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate

5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Downstream raw materials:

5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [4-(3-chloro-phenyl)-2-methylthiazol-5-yl]-amide

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